N-Methyl-N-(pyridine-2-yl)formamide → 4,5-Diphenyloxazole-2-carbaldehyde

Participants

Reaction Steps

n-BuLi (361 mg, 5.65 mmol) was added to a stirred and cooled (−78° C.) solution of 4,5-diphenyloxazole (500 mg, 2.26 mmol) in dry THF. The stirring was continued for 30 min at −78° C., and N-methyl-N-(pyridin-2-yl)formamide (461 mg, 3.39 mmol) was added. The resulting solution was stirred at −78° C. for 1 h, then quenched with H2O. The mixture was extracted with EtOAc (3×20 mL), and the combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by column chromatography to afford the desired product 4,5-diphenyloxazole-2-carbaldehyde (372 mg) as an orange oil.

Provenance & Evidence