N-bromobutanimide → 5-Cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester

Participants

Reaction Steps

A solution of 2-acetyl-4-cyclohexyl-but-2-enoic acid ethyl ester (1.79 g, 7.52 mmol) in 40 mL CCl4 was added to a slurry of NBS (1.338 g, 7.52 mmol) in 40 mL CCl4. The mixture was refluxed under argon for 12 hours, stirred at room temperature for 68 hours and then cooled in an ice bath. The precipitated solid was filtered off and the filtrate was evaporated to an oil that was purified by short-path distillation (165-185° C., 1 mm Hg) yielding 5-cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester (1.36 g, 77%).

Provenance & Evidence