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CAS No. : | 2107-70-2 | MDL No. : | MFCD00002774 |
Formula : | C11H14O4 | Boiling Point : | - |
Linear Structure Formula : | C6H3(OCH3)2CH2CH2COOH | InChI Key : | LHHKQWQTBCTDQM-UHFFFAOYSA-N |
M.W : | 210.23 | Pubchem ID : | 75019 |
Synonyms : |
|
Chemical Name : | 3-(3,4-Dimethoxyphenyl)propionic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 75℃; for 1.5h; | To a solution of 3-(3,4-dimethoxyphenyl)-propionic acid (0.50 g, 2.38 mmol) in 10 mL THF, (CH3)2SBH3 (0.3 mL, 3.57 mmol) was added at 0 C and the mixture was stirred at 75 C for 1.5 h. After the completion of the reaction, excess of (CH3)2SBH3 was quenched by addition of CH3OH at 0 C and then the solvent was evaporated in vacuo. The product was used in the following step without further purification (0.47 g, 100%). 'H NMR (300 MHz, CDCb) d: 6.80 - 6.71 (m, 3H, AT-H), 3.85 (s, 3H, -OC//3), 3.84 (s, 3H, -OC//3), 3.66 (t, = 6.4 Hz, 2H, -C//2OH), 2.64 - 2.62 (m, 2H, -C//2CH2CH2OH), 1.91 - 1.81 (m, 2H, -CH2C//2CH20H).13C NMR (75 MHz, CDCI3) d: 148.9, 147.2, 134.5, 120.2, 11 1.8, 1 1 1.3, 62.3, 56.0, 55.9, 34.5, 31.8. MS m/z: 196.91 (M+H)+, 218.99 (M+Na)+, 414.67 (2M+Na)+ |
92% | With dimethylsulfide borane complex; In tetrahydrofuran; at 0℃; for 4h;Inert atmosphere; | To a solution of 3-(3,4-dimethoxyphenyl)propanoic acid (4.2 g, 20 mmol) in THF (20 mL) was added BH3-DMS (10M, 2.2 mL, 22 mmol) and the reaction was stirred at 0 oC under N2 for 4 hrs. The reaction mixture was quenched with MeOH (5 mL) and concentrated to dryness in vacuum. After that, the dry mixture was poured into H2O (100 mL) and extracted with DCM (50 mL x 3). The combined DCM layers were washed with brine (100 mL), dried over Na2SO4 and concentrated to give 3-(3,4-dimethoxyphenyl)propan-1-ol (3.6 g, yield: 92%) as a colorless oil. |
88.6% | With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 60℃; for 10h; | Compound 3a (11.0 g, 52.3 mmol) was dissolved in 80 ml of tetrahydrofuran and precooled in a 0 C low temperature bath. willSodium borohydride (5.9 g, 157.0 mmol) was added portionwise to the above reaction mixture, and then iodine (13.3 g, 52.3 mmol) in tetrahydrofuran (40 ml) was slowly added dropwise to the reaction mixture. The iodine was consumed completely and there was no gas overflow, and the reaction solution was transferred to a 60 C oil bath for heating for 10 hours. The reaction was monitored by TLC until compound 3a was completely reacted. 30 ml of methanol was slowly added to the reaction solution at 0 C to quench the reaction. After the reaction mixture was poured into 200 ml of water and extracted with dichloromethane (80 ml) three times, the organic phase was combined, and the organic phase was back-washed with saturated brine. The organic phase was dried over anhydrous sodium sulfate and dried.The crude product was purified by flash silica gel column (PE/EA=12/1) The yield was 88.6%. |
A solution of 6.0 g (28.5 mmol) 3- (3, 4-dimethoxyphenyl) -propionic acid in 120 ml anhydrous THF is cooled to 0 C and treated within 15 minutes with 42.75 ml borane THF complex (1 M solution). Stirring is continued overnight at rt. The resulting clear solution is cooled with an ice/water bath and hydrolyzed by the addition of 100 ml saturated ammonium chloride solution. Extractive work-up with diethyl ether furnishes a colourless oil, which is purified by chromatography (HEXANE/ETHYL acetate) to yield a colourless oil. 1H-NMR (300 MHz, CDC13) : 6.76-6. 80 (m, 1H), 6.70-6. 74 (m, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.67 (t, 2H), 2.62-2. 69 (m, 2H), 1.82-1. 93 (m, 2H). MS: 197 (M+1) + | ||
With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; at 20℃; | Step 2. 3-(3,4-dimethoxyphenyl)propanoic acid was dissolved in THF (100 mL). Borane-dimethyl sulfide complex (2M in diethyl ether, 20 mL, 40 mmol) was added. The reaction mixture was stirred overnight at room temperature. Methanol was added slowly to quench the reaction mixture, then silica was added and the volatiles were removed under reduced pressure. The residue was purified on silica using a heptane to ethyl acetate gradient yielding the product as an oil. This was used as such in the next step.LC-MS: Anal. Calcd. For CnHie03: 196.1 1 ; found 195[M-H] | |
With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; at 20℃; | 10129] Step 2. 3-(3,4-dimethoxyphenyl)propanoic acid was dissolved in THF (100 mE). l3orane-dimethyl sulfide complex (2M in diethyl ether, 20 mE, 40 mmol) was added. The reaction mixture was stirred overnight at room temperature. Methanol was added slowly to quench the reaction mixture, then silica was added and the volatiles were removed under reduced pressure. The residue was purified on silica using a heptane to ethyl acetate gradient yielding the product as an oil. This was used as such in the next step.10130] EC-MS: Anal. Calcd. For C, ,H,503: 196.11; found195[M-H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | N,N-dimethylformamide solution (2 ml) containing <strong>[16582-58-4]2-amino-6-iodobenzothiazole</strong> (100 mg, 0.362 mmol) and 3-(3,4-dimethoxyphenyl)propionic acid (91.4 mg, 0.435 mmol) was added with N,N-diisopropylethylamine (69.4 mul, 0.398 mmol) and O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (180 mg, 0.435 mmol) and stirred over night at room temperature. After completion of the reaction, the solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The solution was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was recrystallized with ethanol and 83 mg of 2-(3-(3,4-dimethoxyphenyl)propanamide)-6-iodobenzothiazole in a yield of 48%. 1H NMR (DMSO-d6): delta 12.42 (s, 1H), 8.37 (s, 1H), 7.72-7.69 (m, 1H), 7.52 (d, J=8.4 Hz, 1H), 6.85-6.83 (m, 2H), 6.75-6.72 (m, 1H), 3.71 (s, 3H), 3.69 (s, 3H), 2.90-2.76 (m, 4H). MS (ESI) Found; 469[M+H] |
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