Dimethyl Sulfoxide → 3-(Pyridin-3-yl)propanal

Participants

Reaction Steps

A solution of oxalyl chloride (2.55 g, 20.1 mmol) in anhydrous DCM (150 ml) was cooled to -78° C. and dimethylsulphoxide (3.77g, 40.1 mmol) added dropwise with stirring. After two minutes, 3(3-pyridyl)-1-propanol (0.625 g, 3.79 mmol) was added and stirring continued for a further fifteen minutes Triethylamine (12.70 ml, 91.2 mmol) was then added and stirring continued for five minutes before allowing the solution to warm to room temperature. Water (150 ml) was added the organic layer separated and the aqueous layer extracted with DCM (2×100 ml). The organic extracts were combined, washed with brine (50 ml), dried over anhydrous magnesium sulphate, filtered and evaporated to give a yellow oil (2.20 g, 90%) which was used directly in the next step.

Provenance & Evidence