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CAS No. : | 5400-79-3 | MDL No. : | MFCD01320352 |
Formula : | C8H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VGJWAMLZUUGEQY-UHFFFAOYSA-N |
M.W : | 156.18 | Pubchem ID : | 223136 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
96% | With thionyl chloride; at 15 - 20℃; | General procedure: To a solution of 3-oxocyclohexane carboxylic acid (63.0g, 0.443mol) in ethanol (950mL), SOCl2 (38.8mL, 0.532mol) was added at 15C. The reaction mixture was stirred at rt overnight, and then evaporated under reduced pressure. The residue was dissolved in CHCl3 (500mL) and stirred with saturated aq NaHCO3 (200mL) for 30min. The layers were separated, and the aqueous layer was extracted with CHCl3 (2×50mL). The combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was distilled under reduced pressure to give 23. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sulfuric acid; at 80℃; for 1h; | General procedure: A catalytic amount of concentrated sulfuric acid (10 drops) was added dropwise to a solution of 3-oxocyclopentanecarboxylic acid (5.0 g, 39.1 mmol) in methanol (50 ml). After 1 hour at 80 C, it was cooled to room temperature. The solvent was concentrated under reduced pressure and removed. To the resulting residue, a small amount of water was added. After adjusting the pH to 8 with saturated aqueous sodium bicarbonate, the mixture was extracted with ethyl acetate (30 ml × 3 times). The organic phases were combined, dried and concentrated to give the title compound (4.5 g, 81%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In acetic acid; at 70℃; for 2h; | Intermediate 1 (123mg), acetic acid (10ml) and ethyl [3-OXOCYCLOPENTANE-1-] carboxylate (135mg) were combined and heated to [70C] under a slight vacuum for 2 hours. After cooling to room temperature the solvent was removed in vacuo and the residue purified by column chromatography on silica to afford the title compound as an off-white solid (154mg, 81%). TLC Rf 0.525 (20% [ETOH/ETOAC).] LCMS [386] [M+H] +, RT 2.95 [MINS. 1H] NMR [300MHZ] (d6-DMSO) 8.35 (1 H, s), 7.95 [(1 H,] 2 x s), 7.35 (2H, s), 6.45 (1 H, d), 4.1 (2H, m), 3.9 (3H, 2 x s), 3.1-2. 9 (4H, m), 2.4-1. 8 (4H, m), 1.4-1. 1 (5H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In water; ethyl acetate; | EXAMPLE 5 1,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester To 250 ml of 80% acetic acid in water, were added 4-phenylmethoxyphenylhydrazine hydrochloride (30 g, 0.12 mole) and 3-oxocyclopentane carboxylic acid ethyl ester (20 g, 0.13 mole). After stirring at ambient temperature for one hour and then at 100 C. for four hours, the mixture was cooled and poured into one liter of water. After stirring for five minutes, the mixture was extracted with ethyl acetate (3*). The organic layer was washed successively with water (2*) and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~48 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick brown oil (24.1 g). Analysis: Calculated for C21 H21 NO3: 75.20%C 6.31%H 4.18%N Found: 74.94%C 6.22%H 4.13%N |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; | A solution of cyclopentanone-3-carboxylic acid (5.00 g, 39 mmol), caesium carbonate (12.82 g, 39 mmol) and ethyl iodide (9.12 g, 4.75 ml, 58.5 mmol) in DMF (50 ml) was stirred at RT for 18 h. The mixture was then concentrated i. vac., the residue was taken up in toluene, the mixture was concentrated again and 2 N hydrochloric acid and EtOAc were then added. The aq. phase was extracted with EtOAc (3×30 ml) and the combined organic phases were washed with aq. sodium thiosulfate soln. The organic phase was dried with Na2SO4 and concentrated i. vac.Yield: 4.34 g (71%) |
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