Benzyl 2-cyclopentyl-2-hydroxyacetate → Benzyl 2-keto-2-cyclopentylacetate

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Reaction Steps

A Dess-Martinn reagent (5.8 g, 13.67 mmol) was added to a solution of benzyl 2-cyclopentyl-2-hydroxyacetate (2.0 g, 8.54 mmol) in dichloromethane (30 ml) at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was quenched with 10% sodium thiosulfate and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate and saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a light yellow oil (1.8 g, yield 90%).

Provenance & Evidence