Methyl pyruvate → HCID 18549820, compound

Participants

Reaction Conditions

Reaction Steps

A neat mixture of methyl pyruvate (11.37 mL, 125.9 mmol) and dimethylformamide dimethylacetal (16.72 mL, 125.9 mmol) was stirred at 80° C. for 24 h. The mixture was cooled and concentrated. A portion of the residue (4.00 g, 25.45 mmol) was dissolved in 50 mL of glacial acetic acid and then there was added o-tolylhydrazine hydrochloride (4.44 g, 27.99 mmol). This mixture was stirred at 100° C. for 18 h and then was cooled and concentrated. The residue was dissolved in ethyl acetate, washed with sat'd aq sodium carbonate and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (elution with 2:1 hexanes/ethyl acetate) to afford 3.0 g (55%) of the title compound. 1H NMR (CDCl3) δ7.70 (d, 1H), 7.4-7.2 (m, 4H), 7.00 (d, 1H), 3.71 (s, 3H), 2.00 (s, 3H).

Provenance & Evidence