tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)butyl}benzoate → tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoate

Participants

Reaction Steps

846 mg (3.93 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 1278 mg (3.27 mmol) of tert-butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)-butyl}benzoate in 60 ml of dichloromethane, and the mixture is stirred at room temperature for 12 hours. After complete conversion, 5 g of silica gel are added and the solvent is carefully removed to dryness under reduced pressure. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). This gives 1080 mg (85% of theory) of a colorless oil.

Provenance & Evidence