Dimethyl Sulfoxide → 4-Ethynylcyclohexane-1-carbaldehyde

Participants

Reaction Steps

Oxalyl chloride (354 μl.) was dissolved in dry dichloromethane (3 ml.) at -70° under nitrogen. Dimethyl sulphoxide (650 μl) in dichloromethane (3 ml.) was then added. After stirring for 5 minutes a solution of 4-ethynylcyclohexylmethanol (0.5 g.) in dichloromethane (5 ml.) was added dropwise over 5 minutes. The reaction mixture was stirred for 30 minutes at -70° before triethylamine (2.5 ml.) was added. After warming to 25° over 3 hours, water was added and the organic phase separated, washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine, and dried. Evaporation gave 4-ethynylcyclohexanecarboxaldehyde as a colourless oil.

Provenance & Evidence