Ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate → Ethyl 6-(4-cyanobenzyl)-7-oxoheptanoate

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Reaction Steps

A solution of 4.6 g (15.90 mmol) of ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate from Example 110A in 250 ml of dichloromethane is mixed with 4.11 g (19.08 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 hours. After conversion is complete, 10 g of silica gel are added, and the solvent is cautiously concentrated to dryness in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). 4.09 g (14.23 mmol, 89% yield) of a colorless solid are obtained.

Provenance & Evidence