Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate → Methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoate

Participants

Reaction Steps

320 mg (1.48 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 400 mg (1.24 mmol) of methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate from Example 48A in 7 ml of dichloromethane, and the mixture is stirred at room temperature for 5 hours. After conversion is complete, about 1 g of silica gel is added, and the solvent is removed in vacuo to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 302 mg (90% purity, 69% of theory) of a colourless solid are obtained.

Provenance & Evidence