Potassium Carbonate → Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}propanoate

Participants

Reaction Steps

To a solution of ethyl 3-[3,4-difluoro-5-((1S)-1-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl]propanoate (22.5 g, 52.5 mmol) in absolute ethanol (430 mL) was added potassium carbonate (7.27 g, 52.6 mmol) and the reaction was stirred at RT for 4 days. The reaction was concentrated and diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification by column chromatography (0-25% ethyl acetate:hexane) afforded the desired product (11.07 g, 82%).

Provenance & Evidence