ethyl 2,2,3,3,3-pentafluoropropanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 2,2,3,3,3-pentafluoropropionate (10.99 grams, 57.2 mmol) was dissolved in anhydrous methanol (57 ml) and cooled in an argon atmosphere to −60° C. Sodium borohydride (2.16 g, 57.2 mmol) was added in four portions. After the addition was complete, stirring was continued for one hour and the temperature was held below −45° C. The mixture was cooled to −60° C. and 1M hydrochloric acid (172 ml) was added dropwise so that the temperature remained below −45° C. The mixture was slowly warmed to room temperature and extracted with diethylether (3×100 ml). The combined organic phases were washed with water (two times), dried over magnesium sulfate, the solvent was removed under reduced pressure. 9.76 g (50.3 mmol, 88%) were obtained and used directly in the next step. After the addition was held below −45° C The mixture was cooled to −60° C. remained below −45° C The mixture was slowly warmed to room temperature extracted with diethylether (3×100 ml) The combined organic phases were washed with water (two times) dried over magnesium sulfate the solvent was removed under reduced pressure 9.76 g (50.3 mmol, 88%) were obtained

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 2,2,3,3,3-pentafluoropropionate (10.99 grams, 57.2 mmol) was dissolved in anhydrous methanol (57 ml) and cooled under argon to −60° C. Sodium borohydride (2.16 grams, 57.2 mmol) was added in four portions. After the addition was complete, stirring was continued for one hour and the temperature was held below −45° C. The mixture was cooled to −60° C. and 1M hydrochloric acid (172 ml) was added dropwise so that the temperature remained below −45° C. The mixture was slowly warmed to room temperature and extracted with diethylether (3×100 ml). The combined organic phases were washed with water (two times), dried over magnesium sulfate, the solvent was removed under reduced pressure. 9.76 g (50.3 mmol, 88%) were obtained and used directly in the next step. After the addition was held below −45° C The mixture was cooled to −60° C. remained below −45° C The mixture was slowly warmed to room temperature extracted with diethylether (3×100 ml) The combined organic phases were washed with water (two times) dried over magnesium sulfate the solvent was removed under reduced pressure 9.76 g (50.3 mmol, 88%) were obtained

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl acetate (20.26 g, 0.23 mole) and sodium metal (2.3 g, 0.10 g-atom) was added to ethyl pentafluoropropionate (20.26 g, 0.23 mole) and the mixture was refluxed with stirring until sodium metal was dissolved. After sodium metal was dissolved, dry diethyl ether (100 ml) was added and the solution was further reacted under reflux overnight. After completion of the reaction, the solvent was evaporated under reduced pressure and the resulting residue was made acidic with 50 ml of 15% sulfuric acid, while it was cool. The solution was extracted with diethyl ether and the ether layer was dried with anhydrous sodium sulfate. Diethyl ether was then distilled off by distilling at atmospheric pressure using a fractionating column packed with Raschig ring and the resulting residue was further distilled under reduced pressure to give 9.90 g (42.3%) of the title compound as a colorless liquid, b.p. 77°-78° C./80 mmHg. The structure of this compound was confirmed by IR and NMR. the mixture was refluxed was dissolved the solution was further reacted under reflux overnight After completion of the reaction the solvent was evaporated under reduced pressure was cool The solution was extracted with diethyl ether the ether layer was dried with anhydrous sodium sulfate Diethyl ether was then distilled off by distilling at atmospheric pressure the resulting residue was further distilled under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl acetate (20.26 g, 0.23 mole) and sodium metal (2.3 g, 0.10 g-atom) was added to ethyl pentafluoropropionate (20.26 g, 0.23 mole) and the mixture was refluxed with stirring until sodium metal was dissolved. After sodium metal was dissolved, dry diethyl ether (100 ml) was added and the solution was further reacted under reflux overnight. After completion of the reaction, the solvent was evaporated under reduced pressure and the resulting residue was made acidic with 50 ml of 15% sulfuric acid, while it was cool. The solution was extracted with diethyl ether and the ether layer was dried with anhydrous sodium sulfate. Diethyl ether was then distilled off by distilling at atmospheric pressure using a fractionating column packed with Raschig ring and the resulting residue was further distilled under reduced pressure to give 9.90 g (42.3%) of the title compound as a colorless liquid, b.p. 77°-78° C./80 mmHg. The structure of this compound was confirmed by IR and NMR. the mixture was refluxed was dissolved the solution was further reacted under reflux overnight After completion of the reaction the solvent was evaporated under reduced pressure was cool The solution was extracted with diethyl ether the ether layer was dried with anhydrous sodium sulfate Diethyl ether was then distilled off by distilling at atmospheric pressure the resulting residue was further distilled under reduced pressure