1-(5-Methyl-[1,2,4]oxadiazol-3-yl)-ethanone → HCID 58221804, compound

Participants

Reaction Steps

To a solution of ethynylmagnesium bromide (0.5 M in THF, 800 mL, 400 mmol) at 0° C. was added 1-(5-methyl-1,2,4-oxadiazol-3-yl)ethanone (33.5 g, 266 mmol) in THF (533 mL) slowly. The reaction was allowed to warm to room temperature and stirred for 5 hours. After being quenched with saturated NH4Cl (750 mL) at 0° C., the THF was removed in vacuo and the aqueous residue was extracted with ethyl acetate (600 mL×2). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give dark brown oil. The dark brown oil was purified by silica gel column chromatography use 10% of ethyl acetate in hexanes as eluent to give the title compound (36 g, 89%), 1H NMR (CDCl3, 400 MHz): delta 3.93 (s, 1H), 2.63 (s, 1H), 2.61 (s, 3H), 1.91 (s, 3H).

Provenance & Evidence