Diazomethane → 1-(2-(4-Fluorophenyl)oxazol-4-yl)ethanone

Participants

Reaction Steps

A solution of 2-(4-fluorophenyl)oxazole-4-carbaldehyde (400 mg, 2.09 mmol) in dry chloroform (5 mL) was cooled to 0° C. and a freshly prepared solution of diazomethane in ether (20 mL) was added. The reaction mixture was stirred for 1 h and quenched with 10% aqueous NaHCO3 solution. The crude product was extracted with CH2Cl2 and the combined extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5-8% EtOAc in petroleum ether) to afford 1-(2-(4-fluorophenyl)oxazol-4-yl)ethanone (250 mg, yield 58%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 8.12-8.09 (m, 2H), 7.21-7.17 (t, J=8.7 Hz, 2H), 2.60 (s, 3H). MS (ESI) m/z: Calculated for C11H8FNO2: 205.05. found: 205.9 (M+H)+.

Provenance & Evidence