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[ CAS No. 105601-04-5 ] {[proInfo.proName]}

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Chemical Structure| 105601-04-5
Chemical Structure| 105601-04-5
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Product Details of [ 105601-04-5 ]

CAS No. :105601-04-5 MDL No. :MFCD08272688
Formula : C10H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :GQZXRLWUYONVCP-UHFFFAOYSA-N
M.W : 165.23 Pubchem ID :409441
Synonyms :

Safety of [ 105601-04-5 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P273-P280-P301+P310-P305+P351+P338-P310 UN#:2923
Hazard Statements:H301-H318-H412 Packing Group:Ⅲ
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Application In Synthesis of [ 105601-04-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 105601-04-5 ]

[ 105601-04-5 ] Synthesis Path-Downstream   1~14

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  • [ 129052-92-2 ]
  • [ 105601-04-5 ]
YieldReaction ConditionsOperation in experiment
60% With sulfuric acid; DL-methionine; In water; at 110 - 120℃; for 28h; Experimental procedure: To the solution of 50 % sulfuric acid in water (400.0 [ML),] was added at 10 to 15 C temperature, DL-methionine (124.9 gm, 0.837 moles) and stirred for 15 minutes. To this solution, was added [[1- (3-METHOXYPHENYL)] ethyl] dimethylamine (100.0 gm, 0.553 moles) at 10 to 15 C temperature within 2 hours and stirred for 30 minutes. Reaction mixture was then heated to 110 to 120C temperature for 28 hours. The reaction mixture was diluted with water, basified to pH 8.5 to 9.0 using ammonia solution and extracted with dichloromethane. Organic extract was then washed with water, charcoalized and concentrated. Hexane was then added to the residue and crude product filtered. b) Purification: Crude product was recrystallized from diisopropylether to give pure [1- (3- hydroxyphenyl) ethyl] dimethylamine (55.0 gm, 60 % yield, Purity->99%) melting range: 85 to [86C] temperature)
With hydrogen bromide; In water; at 145 - 150℃; for 12h;Heating / reflux; Preparation of 3- (L-DIMETHYLAMINOETHYL) PHENOL (IV) according to Literature 3 94 g of [1- (3-METHOXYPHENYL) ETHYL] dimethylamine (V) are dissolved in 285 ml of azeotropic hydrobromic acid and the resulting solution is refluxed under stirring using a reflux condenser for 12 hours (bath temperature 145-150 C). During boiling, the reaction mixture darkens. The solution is then left to cool down to room temperature. Excess hydrobromic acid is evaporated using a rotary vacuum evaporator and the evaporation residue is dissolved in 200 ml of water. The solution is extracted with 3x 100 ML ETHYLACETATE. The aqueous fraction is then gradually alkalized with the saturated solution of sodium carbonate with constant stirring (foam creation). The solution becomes milky turbid and it is extracted with 3x 200 ml ethylacetate. The ethylacetate fraction is shaken out lx with water, lx with brine and dried with anhydrous magnesium sulfate. Activated carbon is added before filtering off the desiccant and the desiccant along with the carbon are filtered off. The ethylacetate solution of compound (IV) is used for the next step.
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  • [ 624-83-9 ]
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  • [ 624-83-9 ]
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  • [ 74-88-4 ]
  • [1-(3-hydroxy-phenyl)-ethyl]-trimethyl-ammonium; iodide [ No CAS ]
  • 8
  • [ 42252-34-6 ]
  • [ 105601-04-5 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate; In acetonitrile; at 70 - 80℃; Condensation reaction of 3-(l-dimethylaminoethyl) phenol (10 gm) and ethylmethylcarbamoyl chloride (10gm) was carried in the presence of potassium carbonate (25 gm) and acetonitrile (150 ml) at 70-80 C. After completion of reaction, the reaction mixture was quenched in water (250 ml) at 30-35 C and extracted in ethyl acetate (100ml). Evaporation of ethyl acetate gave the desired compound in 70% yield. Yield: 80-85 gms. %Yield: 66.0% HPLC Purity: 99%.
b) Preparation of 3-(1-(dimethylamino)ethyl)phenyl ethyl-(methyl) carbamate (rivastigmine base) An amount of 5.25 g (30.0 mmol) of 3-(1-dimethylaminoethyl)-phenol was dissolved in 70 ml of acetonitrile. To the solution was slowly added 1.30 g (32.5 mmol) of sodium hydride and stirred for 30 minutes. 6.20 g (51 mmol) of ethyl(methyl)-carbamic chloride were slowly added to the solution. The reaction mixture was stirred for 20 hours. The mixture was filtered and concentrated. 100 ml of water were added and the pH was adjusted with 0.1 M NaOH to pH 12, followed by extraction with ether (3x100 ml). The organic layer was then washed with 100 ml of brine, dried over sodium sulfate, filtered and concentrated. 6.20 g of an oily residue of rivastigmine base were obtained.
An amount of 1.1 g (27.5 mmol, 60 %, 1.05 mole) of sodium hydride suspended in 15 ml of acetonitrile was added to 1.0 mole of the above obtained 3-(1-dimethylaminoethyl)phenol (as acetonitrile solution) within a period of 30 minutes while maintaining the reaction mixture at the room temperature. After the addition of sodium hydride an amount of 3.1 ml (3.44 g, 97 % 27.5 mmol, 1.05 molar equivalent) of ethyl(methyl)-carbamic chloride were added within a period of 30 minutes. The reaction mixture was stirred for 2 hours at room temperature and then the solvent was removed under vacuum at 50 mbar and 50C. 55 ml of ether and 35 ml of water were added to the residue, the pH was set to 11 with 0.1 M NaOH and stirred for 20 minutes. The layers were separated. The water phase was washed with 25 ml of ether and the organic phases were combined, dried with 2.0 g of Na2SO4 and filtered. The filtrate was concentrated to obtain 6.4 g of an oily substance of 3-(1-(dimethylamino)ethyl)phenyl ethyl(methyl)carbamate. Yield from 1-(3-hydroxyphenyl)-N,N-dimethyl-ethanaminium chloride was 85 %, purity of the product 97.7 area %.
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  • [ 2747-08-2 ]
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  • 2-(3-(1-(dimethylamino)ethyl)phenoxy)-5,6-dimethoxy-2,3-dihydro-1H-indan-1-one [ No CAS ]
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  • [ 50-00-0 ]
  • [ 923035-06-7 ]
  • [ 105601-04-5 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen;nickel; In methanol; at 80℃; under 7355.72 Torr; for 3 - 4h;Product distribution / selectivity; Example 2: Preparation of alpha-m-hydroxy phenylethyldimethylamine; N-methylation was carried out on alpha-m-hydroxy phenylethylmethylamine (25g) with Paraformaldehyde (15g) in presence of Raney Nickel (3Og) in methanol(500ml) at 80C and 10kg /cm2 of lrydrogen pressure in an autoclave. After 3-4 hours the product was isolated by removing Raney nickel and concentrating the filtrate. The product was further <n="9"/>purified by dissolving the crude product in Toluene (50ml) and is crystallized by slow addition of Petroleum ether (150ml). Pure alpha-m-hydroxy phenylethyldimethylarnine is isolated (23g, Yield: 85%, purity 98%) by filtration.Characterization data:1H-NMR (DMSO): 9.25(1H, s), 7.05(1H, t), 6.60(3H, m), 3.08(1H5 q), 2.05(6H, s),1.19(3H, d)13C-NMR (DMSO): 158.0, 146.7, 129.8, 118.7, 114.8, 114.5, 65.8, 43.6, 20.9.Mass(Methanol) : 166.2 (M+l); Example 4: Preparation of alpha-m-hydroxy phenylethyldimethylamine; N-methylation was carried out on alpha-m-hydroxy phenylethylmethylamine (25g) with Paraformaldehyde (15g) in presence of Raney Nickel (30g) in methanol (500ml) at 80C and 10kg /cm of hydrogen pressure in an autoclave. After 3-4 hours the product was isolated by removing Raney nickel and concentrating the filtrate. The product was further purified by dissolving the crude product in Toluene (50ml) and is crystallized by slow addition of Petroleum ether (150ml). Pure alpha-m-hydroxy phenylethyldimethylamine is isolated (23g, Yield: 85%, purity 98%) by filtration.Characterization data: 1H-NMR (DMSO): 9.25(1H, s), 7.05(1H, t), 6.60(3H, m), 3.08(1H, q), 2.05(6H, s), 1.19(3H, d) 13C-NMR (DMSO): 158.0, 146.7, 129.8, 118.7, 114.8, 114.5, 65.8, 43.6, 20.9. <n="10"/>Mass(Methanol) : 166.2 (M+l)
85% With hydrogen;Raney nickel; In methanol; at 80℃; under 7355.72 Torr; for 3 - 4h;Product distribution / selectivity; Example 2 Preparation of alpha-m-hydroxy phenylethyldimethylamine N-methylation was carried out on alpha-m-hydroxy phenylethylmethylamine (25 g) with Paraformaldehyde (15 g) in presence of Raney Nickel (30 g) in methanol (500 ml) at 80 C. and 10 kg/cm2 of hydrogen pressure in an autoclave. After 3-4 hours the product was isolated by removing Raney nickel and concentrating the filtrate. The product was further purified by dissolving the crude product in Toluene (50 ml) and is crystallized by slow addition of Petroleum ether (150 ml). Pure alpha-m-hydroxy phenylethyldimethylamine is isolated (23 g, Yield: 85%, purity 98%) by filtration. Characterization Data: 1H-NMR (DMSO): 9.25(1H, s), 7.05(1H, t), 6.60(3H, m), 3.08(1H, q), 2.05(6H, s), 1.19(3H, d) 13C-NMR (DMSO): 158.0, 146.7, 129.8, 118.7, 114.8, 114.5, 65.8, 43.6, 20.9. Mass (Methanol): 166.2 (M+1) Example 4Preparation of alpha-m-hydroxy phenylethyldimethylamineN-methylation was carried out on alpha-m-hydroxy phenylethylmethylamine (25 g) with Paraformaldehyde (15 g) in presence of Raney Nickel (30 g) in methanol (500 ml) at 80 C. and 10 kg/cm2 of hydrogen pressure in an autoclave. After 3-4 hours the product was isolated by removing Raney nickel and concentrating the filtrate. The product was further purified by dissolving the crude product in Toluene (50 ml) and is crystallized by slow addition of Petroleum ether (150 ml). Pure alpha-m-hydroxy phenylethyldimethylamine is isolated (23 g, Yield: 85%, purity 98%) by filtration.Characterization Data:1H-NMR (DMSO): 9.25(1H, s), 7.05(1H, t), 6.60(3H, m), 3.08(1H, q), 2.05(6H, s), 1.19(3H, d)13C-NMR (DMSO): 158.0, 146.7, 129.8, 118.7, 114.8, 114.5, 65.8, 43.6, 20.9.Mass (Methanol): 166.2 (M+1)
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  • [ 923035-06-7 ]
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YieldReaction ConditionsOperation in experiment
85% With formaldehyd; hydrogen; In methanol; aluminum nickel; toluene; Petroleum ether;Product distribution / selectivity; Example 4 Preparation of alpha-m-hydroxy phenylethyldimethylamine N-methylation was carried out on alpha-m-hydroxy phenylethylmethylamine (25 g) with Paraformaldehyde (15 g) in presence of Raney Nickel (30 g) in methanol (500 ml) at 80 C. and 10 kg/cm2 of hydrogen pressure in an autoclave. After 3-4 hours the product was isolated by removing Raney nickel and concentrating the filtrate. The product was further purified by dissolving the crude product in Toluene (50 ml) and is crystallized by slow addition of Petroleum ether (150 ml). Pure alpha-m-hydroxy phenylethyldimethylamine is isolated (23 g, Yield: 85%, purity 98%) by filtration. Characterization Data: 1H-NMR (DMSO): 9.25(1H, s), 7.05(1H, t), 6.60(3H, m), 3.08(1H, q), 2.05(6H, s), 1.19(3H, d) 13C-NMR (DMSO): 158.0, 146.7, 129.8, 118.7, 114.8, 114.5, 65.8, 43.6, 20.9. Mass (Methanol): 166.2 (M+1)
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  • [ 3144-16-9 ]
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  • [ 798561-06-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 80℃; for 0.166667 - 1h;Resolution of racemate;Purification / work up; Example 5Resolution of dl-alpha-m-HydroxyphenylethylmethylamineRacemic dl-alpha-m-Hydroxyphenylethylmethylamine (20 g) dissolved in Ethanol (300 ml) was added d-camphorsulphonic acid (33 g), and the reaction mixture was heated to 40-80 C. for 10-60 mins, and then Ethanol was distilled out completely under vacuum, the same operation was repeated twice with Ethanol (100 ml×2). Residual mass was added Ethyl acetate (250 ml) and distilled out. The residual mass was added i-Propanol (60 ml) and stirred for 2-3 days at 0-25 C. The precipitated solid was filtered (10-20 g).The camphorsulfonate thus obtained was dissolved in Sod. Carbonate soln and then extracted with Ethyl acetate (2×25 ml). Combined organic layer was distilled out and Cyclohexane (50 ml) was added to the residual mass and stirred for 10-30 mins. The solid material was then filtered and dried under vacuum at 40-80 C. (5-10 g) (m.p. 171 C. [alpha]D -68.0; c=5.0 in C5H5N)
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  • [ 851086-95-8 ]
  • [ 139306-10-8 ]
YieldReaction ConditionsOperation in experiment
Example 5: Resolution of dl-alpha-m-Hydroxyphenylethymethylamine:; Raceniic dl-alpha-m-Hydroxyphenylethylmethylamine (20 g) dissolved in Ethanol (300 ml) was added d-camphorsulphonic acid (33 g), and the reaction mixture was heated to 40- 8O0C for 10-60 mins, and then Ethanol was distilled out completely under vacuum, the same operation was repeated twice with Ethanol (100ml X 2). Residual mass was added Ethyl acetate (250 ml) and distilled out. The residual mass was added z-Propanol (60 ml) and stirred for 2-3 days at 0-25C. The precipitated solid was filtered (10-20 g). The camphorsulfonate thus obtained was dissolved in Sod. Carbonate soln and then extracted with Ethyl acetate (2x 25ml). Combined organic layer was distilled out and Cyclohexane (50ml) was added to the residual mass and stirred for 10-30 mins. The solid material was then filtered and dried under vacuum at 40-80C (5-1Og) (m.p. 1710C [alpha] D - 68.0; c= 5.0 in C5H5N)
  • 14
  • [ 105601-04-5 ]
  • [ 7693-46-1 ]
  • [ 948829-23-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at -78 - 5℃; for 3.08333 - 3.58333h;Product distribution / selectivity; Comparative example 1; Reaction scheme :[0047] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C.[0048] 0.92 g Triethylamine was added. A solution of 1.22 g 4-nitrophenyl chloroformate in 5 ml dichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The solution was stirred at -78C. Reaction progress was monitored by HPLC. After 3 hours at -780C, HPLC showed that there was still starting material present. A second addition of 0.61 g 4-nitrophenyl chloroformate in 2 ml dichloromethane (dried on CaCl2) was made. After 30 min at -78, the starting material was completely converted (ace. to HPLC). [0049] 715 mg N-Ethylmethylamine was added and the yellow reaction mixture was allowed to warm slowly to O0C. The reaction mixture was stirred for 40 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether. <n="15"/>[0050] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~10-l 1 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 1.4 g (93%), yellow oilHPLC : 97.6% purity1H-NMR: confirmed the expected structure; The Comparative example 1 was repeated with the following solvents and reaction temperatures with the following results:; Example 1; Synthesis and isolation of compound VII-Ia-78' 5C[0052] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C. <n="16"/>[0053] 0.92 g triethylamine was added. A solution of 1.22 g4-nitrophenyl chloroformate in 5 mldichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The mixture was stirred at -780C. Reaction progress was monitored with HPLC. After 3 hours at -78C, the reaction mixture was allowed to warm to ambient temperature and was then washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 2.1 g, yellow oilHPLC : 83% purity1H- and 13C-NMR: confirmed the expected structure
With triethylamine; In ethyl acetate; at -20℃; for 3.58333h;Product distribution / selectivity; Comparative example 1; Reaction scheme :[0047] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C.[0048] 0.92 g Triethylamine was added. A solution of 1.22 g 4-nitrophenyl chloroformate in 5 ml dichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The solution was stirred at -78C. Reaction progress was monitored by HPLC. After 3 hours at -780C, HPLC showed that there was still starting material present. A second addition of 0.61 g 4-nitrophenyl chloroformate in 2 ml dichloromethane (dried on CaCl2) was made. After 30 min at -78, the starting material was completely converted (ace. to HPLC). [0049] 715 mg N-Ethylmethylamine was added and the yellow reaction mixture was allowed to warm slowly to O0C. The reaction mixture was stirred for 40 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether. <n="15"/>[0050] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~10-l 1 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 1.4 g (93%), yellow oilHPLC : 97.6% purity1H-NMR: confirmed the expected structure; The Comparative example 1 was repeated with the following solvents and reaction temperatures with the following results:
With triethylamine; In chloroform; at -20℃; for 3.58333h;Product distribution / selectivity; Comparative example 1; Reaction scheme :[0047] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C.[0048] 0.92 g Triethylamine was added. A solution of 1.22 g 4-nitrophenyl chloroformate in 5 ml dichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The solution was stirred at -78C. Reaction progress was monitored by HPLC. After 3 hours at -780C, HPLC showed that there was still starting material present. A second addition of 0.61 g 4-nitrophenyl chloroformate in 2 ml dichloromethane (dried on CaCl2) was made. After 30 min at -78, the starting material was completely converted (ace. to HPLC). [0049] 715 mg N-Ethylmethylamine was added and the yellow reaction mixture was allowed to warm slowly to O0C. The reaction mixture was stirred for 40 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether. <n="15"/>[0050] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~10-l 1 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 1.4 g (93%), yellow oilHPLC : 97.6% purity1H-NMR: confirmed the expected structure; The Comparative example 1 was repeated with the following solvents and reaction temperatures with the following results:
With triethylamine; In acetonitrile; at -20℃; for 3.58333h;Product distribution / selectivity; Comparative example 1; Reaction scheme :[0047] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C.[0048] 0.92 g Triethylamine was added. A solution of 1.22 g 4-nitrophenyl chloroformate in 5 ml dichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The solution was stirred at -78C. Reaction progress was monitored by HPLC. After 3 hours at -780C, HPLC showed that there was still starting material present. A second addition of 0.61 g 4-nitrophenyl chloroformate in 2 ml dichloromethane (dried on CaCl2) was made. After 30 min at -78, the starting material was completely converted (ace. to HPLC). [0049] 715 mg N-Ethylmethylamine was added and the yellow reaction mixture was allowed to warm slowly to O0C. The reaction mixture was stirred for 40 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether. <n="15"/>[0050] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~10-l 1 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 1.4 g (93%), yellow oilHPLC : 97.6% purity1H-NMR: confirmed the expected structure; The Comparative example 1 was repeated with the following solvents and reaction temperatures with the following results:
With triethylamine; In tetrahydrofuran; at -20℃; for 3.58333h;Product distribution / selectivity; Comparative example 1; Reaction scheme :[0047] 1 g 3-(l-Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (dried on CaCl2). The solution was cooled to -780C.[0048] 0.92 g Triethylamine was added. A solution of 1.22 g 4-nitrophenyl chloroformate in 5 ml dichloromethane (dried on CaCl2) was added dropwise over 5 minutes. The solution was stirred at -78C. Reaction progress was monitored by HPLC. After 3 hours at -780C, HPLC showed that there was still starting material present. A second addition of 0.61 g 4-nitrophenyl chloroformate in 2 ml dichloromethane (dried on CaCl2) was made. After 30 min at -78, the starting material was completely converted (ace. to HPLC). [0049] 715 mg N-Ethylmethylamine was added and the yellow reaction mixture was allowed to warm slowly to O0C. The reaction mixture was stirred for 40 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether. <n="15"/>[0050] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~10-l 1 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 1.4 g (93%), yellow oilHPLC : 97.6% purity1H-NMR: confirmed the expected structure; The Comparative example 1 was repeated with the following solvents and reaction temperatures with the following results:

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; ;