3,5-Dimethyl-4-(hydroxymethyl)isoxazole → 3,5-Dimethyl-4-Isoxazolecarbaldehyde

Participants

Reaction Steps

Manganese dioxide (5.48 g, 62.9 mmol) and dichloromethane (20 mL) were added to a solution of 3,5-dimethylisoxazole-4-methanol (prepared according to the literature procedure: Saucy, G.; Scott, J. W. U.S. Pat. No. 3,984,428 Oct. 5, 1976; 1.00 g, 7.9 mmol) in dichloromethane (25 mL). The mixture was stirred at room temperature overnight, then filtered through Celite®, evaporated under reduced pressure and the residual material was chromatographed over silica gel (10% ethyl acetate/hexanes) to give 3,5-dimethylisoxazole-4-carboxaldehyde (365 mg, 37% yield) as a colorless solid.

Provenance & Evidence