Dimethyl Sulfoxide → HCID 86707842, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of oxalyl chloride (23.8 g, 189 mmol) in 100 ml of methylene chloride, DMSO (29.6 g, 380 mmol) was added slowly and the mixture was stirred for 0.5 h at the same temperature. Then, a solution of 2-(1-methoxy-piperidin-4-yl)-ethanol (12 g, 75 mmol) in 50 ml of methylene chloride was added. After stirring for 30 minutes, triethylamine (44 g, 430 mmol) was added to the mixture. After the addition, the reaction mixture was warmed to room temperature and diluted with methylene chloride. The organic solution was washed with water and aqueous NaHCO3. The organic layers was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel. Yield: 11.5 g of (1-methoxy-piperidin-4-yl)-acetaldehyde as an oil.

Provenance & Evidence