Dimethyl Sulfoxide → 5-Methyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Dissolve dimethyl sulfoxide (0.751 mL, 10.6 mmol) in DCM (20 mL) and cool to −78° C. Add oxalyl chloride (0.577 mL, 6.62 mmol) dropwise in DCM (8 mL) and stir for 15 min. Add (5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol (0.501 g, 2.65 mmol) in DCM (20 mL) dropwise and stir for one hr. at −78° C. Add triethylamine (1.85 mL, 13.2 mmol) and warm the mixture to room temperature for one hr. Dilute the mixture with saturated sodium bicarbonate and extract 3 times with DCM. Dry (sodium sulfate) the solution, filter and concentrate to give the title preparation as a white solid (0.496 g, 100%). MS (ES): m/z=188 [M+H]+.

Provenance & Evidence