Methanol → Methyl alpha-methylbenzeneacetate

Participants

Reaction Steps

A solution of 2-(3-chloro-4-dimethylcarbamoylthio)phenyl propionic acid methyl ester (0.106 g; 0.352 mmol) in dry methanol (1.42 mL) was treated with a solution of sodium methoxide in methanol (4.37 M; 0.113 mL; 0.493 mmol). The solution was refluxed for 4 hours and then cooled to room temperature. 3-ethyl-6-(3-bromopropyl)oxy-7-propyl-benz[4,5]isox-azole (0.096 grams; 0.293 mmol) was added and the reaction stirred for 1 hour. The reaction mixture was partitioned between isopropyl acetate and pH 4.0 buffer. The organic layer was dried over magnesium sulfate, filtered and evaporated. Silica gel chromatography afforded the title compound.

Provenance & Evidence