Acetic Anhydride → N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

Participants

Reaction Steps

(2S)-2-[(5-fluoro-2-nitrophenoxy)methyl]oxirane (0.32 g, 1.5 mmol) was dissolved in ethyl acetate (40 ml). Platinum on charcoal (0.15 g) was added, and the mixture was stirred in the atmosphere of hydrogen for 3 h at room temperature and atmospheric pressure. The catalyst was filtered and washed on the filter with ethyl acetate (10 ml). Acetic anhydride (0.31 g, 0.28 ml, 3 mmol) and ethyldi(i-propyl)amine (0.39 g, 0.52 ml, 3 mmol) were added to the solution. The reaction mixture was stirred at room temperature for 3 h, then washed with 1M sodium hydroxide (NaOH) (30 ml) and brine (30 ml), and dried with sodium sulphate (Na2SO4). Evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (from 25 to 75%) afforded the subtitle compound (0.21 g, 0.92 mmol, 61%) as a colourless solid.

Provenance & Evidence