1-(1H-Imidazol-1-yl)ethanone → HCID 66891447, compound

Participants

Reaction Steps

A solution of (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (250 mg, 0.88 mmol) in tetrahydrofuran (2 mL) was added to a suspension of sodium hydride (40% oil dispersion, 70 mg, 1.8 mmol) in tetrahydrofuran (5 mL), followed by the addition of 1-acetylimidazole (145 mg, 1.3 mmol). After five minutes at room temperature, stirring was continued at 60° C. for 20 minutes. After cooling to room temperature, the reaction mixture was quenched with hydrochloric acid (1M, 20 mL) and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give the crude 2-(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.26 g, 0.80 mmol, 91% yield). 1H NMR (400 MHz, CDCl3): 6.73-6.69 (m, 2H), 4.29-4.21 (m, 2H), 4.15-4.13 (m, 2H), 3.79-3.76 (m 2H), 3.62-3.57 (m, 2H), 3.44 (s, 3H), 3.41 (s, 3H), 2.26 (s, 3H); MS (EI) for C16H20FNO5: 326 (MH+).

Provenance & Evidence