Dimethyl Sulfoxide → 1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carbaldehyde

Participants

Reaction Steps

To a stirred solution of oxalyl chloride (92 μL, 1.07 mmol) in DCM (2 mL) at −78° C. is added dropwise a solution of dimethyl sulfoxide (0.15 mL, 2.16 mmol) in DCM (2 mL). After 15 mins a solution of (1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol (0.26 g, 0.79 mmol) in DCM (2 mL) is added dropwise. After another 15 mins, triethylamine (0.425 mL, 3.04 mmol) is added and the reaction is allowed to warm to room temperature. Stirring is continued for 18 h. The mixture is diluted with water and extracted with DCM. The organic layers are combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.26 g (99%) of 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carbaldehyde. m/z=331.

Provenance & Evidence