Hydrochloric Acid → Benzyl 2(R)-benzyl-4-oxopentanoate

Participants

Reaction Steps

A suspension of 500 mg (5 mmoles) of cuprous chloride and 180 mg (1 mmole) of palladium chloride in a mixture of 5 ml of dimethylformamide and 0.6 ml of water was stirred for 1 hour under an atmosphere of oxygen. At the end of this time, 1.41 g(5.03 mmoles) of benzyl 2(S)-benzyl-4-pentenoate (prepared as described in Preparation 18) was added to the mixture. The mixture was then stirred for an additional 5 hours at room temperature and under an atmosphere of oxygen, after which the reaction mixture was poured into 100 ml of 1N aqueous hydrochloric acid, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 5:1 by volume mixture of hexane and ethyl acetate as eluent), to give 1.28 g (yield 86%) of the title compound as a colorless oily substance.

Provenance & Evidence