Sodium Thiosulfate → N-(4-cyanophenyl)-3-methyl-5-oxopentanamide

Participants

Reaction Steps

To a solution of the compound obtained in Step 1 (435 mg, 1.87 mmol) in acetonitrile (10 mL) was added Dess-Martin Periodinane (953 mg, 2.25 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 80% ethyl acetate/hexane) to give crude N-(4-cyanophenyl)-3-methyl-5-oxopentanamide (113 mg, 0.492 mmol, 26.3%) as a white powder.

Provenance & Evidence