Dimethyl Sulfoxide → 4-Nitropicolinaldehyde

Participants

Reaction Conditions

Reaction Steps

To cooled solution of oxalyl chloride (0.533 g, 4.18 mmol) in DCM (2 mL) at −78° C. under nitrogen was added dimethyl sulfoxide (0.593 mL, 8.37 mmol) dropwise. After 30 minutes (4-nitro-pyridin-2-yl)-methanol (17)(0.129, 0.837 mmol) in DCM (2 mL) was added dropwise maintaining temperature at −78° C. After 2 hours the mixture was warmed to −55° C. Triethylamine (1.74 mL, 12.55 mmol) was then added and the mixture allowed to warm to room temperature over 2 hours. Brine (10 mL) was then added and the mixture extracted with DCM (4×10 mL). The combined organics were then dried over MgSO4 and concentrated in vacuo to an oil. The material was used directly without need for purification assuming quantitative conversion.

Provenance & Evidence