Hydrochloric Acid → (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Participants

Reaction Steps

In 2 liter of methanol was dissolved 50 g of [(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] 3,5-dinitrobenzoate and, at room temperature, 255 ml of 1N aqueous solution of sodium hydroxide was added dropwise to the solution. The reaction mixture was stirred at room temperature for 1 hour, neutralized with 127 ml of 1N aqueous solution of hydrochloric acid and removed off methanol under reduced pressure. To the residue were added 1 liter of ethyl acetate and 200 ml of water. The resultant mixture was extracted with ethyl acetate, and the organic phase was washed with 200 ml of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and distilled off the solvent under reduced pressure. The residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=1:3) to give 25 g of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a pale yellow oily substance.

Provenance & Evidence