Triethylamine → HCID 54536538, compound

Participants

Reaction Steps

Pivaloyl chloride (23.5 g, 195 mmol) was added dropwise to a stirred solution of 3,4-dimethoxycinnamic acid (40 g, 192 mmol) and triethylamine (54.4 ml, 390 mmol) in N,N-dimethylformamide (600 ml) at -30° C. To the resulting mixture was added a solution of N-methylhydroxylamine hydrochloride (15.9 g, 190 mmol) in N,N-dimethylformamide (50 ml). The mixture was allowed to warm slowly to room temperature. Ethyl ether (600 ml) was added, and the precipitated triethylamine hydrochloride filtered off. The filtrate was concentrated in vacuo to leave a yellow oil, which was dissolved in 400 ml ethyl acetate. Additional triethylamine hydrochloride was removed by filtration, and the filtrate seeded and allowed to stand at room temperature overnight. The precipitated product was collected by filtration, dried in vacuo, and recrystallized from methanol-water to provide 19.0 g of the named compound as a white powder, mp 149.5°-150.5° C.

Provenance & Evidence