Thionyl Chloride → 7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Participants

Reaction Steps

5-(2,4-Dimethoxy-benzyl)-7-oxo-2-phenyl-4,5,6,7-tetrahydro-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (1.05 g, 2.49 mmol), was dissolved in 17 mL of anhydrous dichloromethane. To the solution was added 272 μL of thionyl chloride, and the reaction was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 0.20 g of the title compound as a white solid. MS: (−) m/z 269.1 (M−1).

Provenance & Evidence