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

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.

1. customremoved off methanol under reduced pressure
2. additionTo the residue were added 1 liter of ethyl acetate and 200 ml of water
3. extractionThe resultant mixture was extracted with ethyl acetate
4. washthe organic phase was washed with 200 ml of a saturated aqueous solution of sodium chloride
5. dry with materialdried over magnesium sulfate
6. distillationdistilled off the solvent under reduced pressure
7. customThe residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=1:3)

ORD record

ord-542e5d783b5648eabfdd2b9c12cbb297

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05814324