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

Participants

Reaction Conditions

Reaction Steps

Dimethylsulphoxide (18.9 ml) in dry dichloromethane (120 ml) was added over20 minutes to a stirred solution of oxalyl chloride (11.55 ml) in dry dichloromethane (225 ml) at -70° C. The mixture was stirred at -70° C. for 10 minutes and then a solution of 3-(3-pyridyl)propanol(16.56 g) in dry dichloromethane (120 ml) was added with stirring over 20 minutes. Stirring was continued at -70° C. for a further 20 minutesand then triethylamine (50.55 ml) was added dropwise and the temperature was allowed to rise to room temperature. Water (200 ml) was added and the layers were separated. The organic layer was washed twice with water, dried (MgSO4) and evaporated. The residue was distilled to give the title compound as an oil (8.80 g), b.p. 88°-92° C. @ 0.3 mm., Rf. 0.15 (SS2). δ(CDCl3): 2.80(3H,t), 2.93(3H,t), 7.18-7.21 (1H,m), 7.50(1H,d), 8.40-8.45(2H,m), 9.80(1H,s).

Provenance & Evidence