Dimethyl Sulfoxide → 7-(p-Toluenesulfonyloxy)-2-heptenal

Participants

Reaction Steps

To a solution of oxalic chloride (19.9 ml, 0.229 mol) in dichloromethane (400 ml) was added dimethyl sulfoxide (32.4 ml, 0.457 mol) at -78° C. and the mixture was stirred for 15 minutes. To the reaction mixture was added dropwise over 30 minutes a solution of 5-hydroxypentyl p-toluenesulfonate (19.65 g, 76.16 mmol) in dichloromethane (50 ml) and the mixture was stirred for 15 minutes and then triethylamine (95.5 ml, 0.686 mol) was added dropwise over 10 minutes and allowed to rise to room temperature. After chloroform (200 ml) was added to the reaction mixture, it was washed successively with 5% aqueous hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and saturated aqueous sodium chloride (200 ml), dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 7-(p-toluenesulfonyloxy)-2-heptenal (24.5 g). This aldehyde was used for the subsequent reaction without purification.

Provenance & Evidence