Dimethyl Sulfoxide → 3-(6-Methyl-2-pyridyl)propanal

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (1.78 g, 22.9 mmol) in dichloromethane (4mL) was added dropwise over 3 min into solution of oxalyl chloride (11.3 mmol) in dichloromethane (6 mL) cooled to -78° C. under nitrogen. The reaction mixture was stirred for 5 min when 3-(6-methyl-2-pyridyl)propanol (1.57 g, 10.4 mmol) in dichloromethane (20 mL) was added over 5 min. The stirring continued for 20 min at -78° C. and triethylamine (8 ml) was added resulting in dark slurry. The cooling bath was removed and after 3 hr, the reaction mixture was quenched with brine followed by dichloromethane extraction (3×). After solvent removal, the dark residue was purified by column chromatography (silica gel, ethyl acetate) yielding a yellow oil (77%). MS (DCI) (M+H)+ at m/z 150.

Provenance & Evidence