Sodium hydride → HCID 61633471, compound

Participants

Reaction Steps

A solution of ethyl 2-(methylideneamino)acetate (1.7 g, 14.77 mmol, 1.00 equiv) was added dropwise to a stirred mixture of sodium hydride (60%, 722 mg, 18.05 mmol, 1.22 equiv) in toluene (30 mL) at 5° C. The mixture was stirred at room temperature for 30 min. 4-cyanobenzoyl chloride (3 g, 18.12 mmol, 1.22 equiv) was then added dropwise at 5° C. The reaction was stirred at room temperature for 12 h then quenched with 30 mL of ice-water mixture. The resulting mixture was extracted with 2×15 mL of ethyl acetate. The combined organic layers was washed with 1×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-30% of ethyl acetate in petroleum ether to give 1.3 g (36%) of ethyl 5-(4-cyanophenyl)oxazole-4-carboxylate as a red solid. 1H-NMR (300 MHz, CDCl3): δ 8.29-8.26 (m, 2H), 8.00 (s, 1H), 7.91-7.77 (m, 2H), 4.48-4.41 (m, 2H), 1.46-1.41 (t, J=7.2 Hz, 3H) ppm.

Provenance & Evidence