Dimethyl Sulfoxide → 6-Methyl-3-pyridinecarboxaldehyde

Participants

Reaction Steps

To a stirred solution of dimethyl sulfoxide (25.3 mL, 0.357 mol) and CH2Cl2 (600 mL) under nitrogen at −78° C. was slowly added oxalyl chloride (16 mL, 0.19 mol). After completion of the addition, the mixture was stirred for additional 10 min. To the resulting solution was added dropwise a solution of (6-methyl-3-pyridyl)methanol (20 g, 0.162 mol) in CH2Cl2 (10 mL), and then the mixture was stirred at −78° C. for 2.5 hr. Triethylamine (110 mL, 0.82 mol) was slowly added at −78° C. and then the mixture was slowly warmed to room temperature and stirred for another 1 hr. The mixture was treated with water and the aqueous phase was extracted with CH2Cl2 (3×500 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel column to afford the title compound.

Provenance & Evidence