4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one → HCID 90462327, compound

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Reaction Steps

A solution of [4-(propan-2-yloxy)phenyl]hydrazine hydrochloride (1 g, 4.93 mmol, 1.00 equiv) and (4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine (1.4 g, 8.08 mmol, 1.64 equiv) in ethanol (20 mL) was refluxed for 3 h. The resulting mixture was cooled to room temperature and concentrated under vacuum. Acetone (10 mL) and 6N hydrochloric acid (10 mL) was added to dissolve the residue and the resulting solution was stirred at room temperature overnight. The reaction was diluted with 100 mL of dichloromethane and then washed with 3×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 3.0-7.0% of methanol in dichloromethane to yield 200 mg (18%) of 1-[4-(propan-2-yloxy)phenyl]-1H-pyrazole-5-carbaldehyde as a yellow oil. LCMS (method A, ESI): RT=1.48 min, m/z=230.9 [M+H]+.

Provenance & Evidence