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

Participants

Reaction Conditions

Reaction Steps

2-(2,4-Difluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl]oxirane (82 g) (sythesized by a method disclosed in the Japanese Laid-Open Publication Hei-04/74168) and 6.3 g of pyridinium p-toluenesulfonte were dissolved in 600 ml of ethanol and the solution was stirred at 55° C. for one hour. The reaction solution was concentrated under reduced pressure. The residue was dissolved in one liter of ethyl acetate and the resulting solution was washed with water (2×200 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=10/1 to 8/1 to 3/1) to give 31.5 g of (1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a pale yellow oil.

Provenance & Evidence