Benzoic Acid → [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate

Participants

Reaction Steps

To a solution of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (16.1 g) in tetrahydrofuran (320 ml) were added triphenylphosphine (63.3 g), benzoic acid (29.5 g) and diethyl azodicarboxylate (42.0 g) under ice-cooling. The mixture was stirred for 6 hours at room temperature under argon atmosphere. To the reaction mixture were added ethyl acetate (800 ml) and water (500 ml). The separated aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water and a saturated saline, dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=15:1→7:1) for purification to give [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate (19.2 g) as a colorless oily substance.

Provenance & Evidence