Sodium Acetate → 2-Benzyloxymethyl-2-benzylthiomethyl-pentanal

Participants

Reaction Steps

2-Benzyloxymethyl-2-benzylthiomethyl-pentan-1-ol (5 g.) was added to a stirred suspension of pyridinium chlorochromate (5 g.) and anhydrous sodium acetate (3.0 g.) in dry dichloromethane (20 ml.) at 0°, under a current of nitrogen. The mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (100 ml.) and the organic solution was decanted off. The oily residue was treated with ether and the combined extracts were evaporated in vacuo. The residue was chromatographed on silica eluting with ethyl acetate:hexane, 1:10. 2-Benzyloxymethyl-2-benzylthiomethyl-pentanal was obtained as a colourless oil (1.9 g.).

Provenance & Evidence