3,4,5-Trimethoxybenzaldehyde → HCID 12193793, compound

Participants

Reaction Steps

72 ml of n-butyllithium solution (1.6M in hexane) were added at -110° to a solution of 11.72 ml (0.115 mol) of ethyl propiolate in 195 ml of tetrahydrofuran/ether/hexane (4:2:1). The mixture was stirred at -110° for 20 minutes and then treated with 15.0 g (76.4 mmol) of 3,4,5-trimethoxybenzaldehyde in 30 ml of tetrahydrofuran. The mixture was thereafter stirred at -78° for 1.5 hours and treated at -30° with 100 ml of saturated ammonium chloride solution and 100 ml of ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:1), whereafter there was obtained ethyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate.

Provenance & Evidence