1-Naphthaldehyde → Ethyl 3-(naphthalen-1-yl)prop-2-enoate

Participants

Reaction Steps

22.4 g(0.10 mol) of triethylphosphonoacetate was dissolved in 500 ml of tetrahydrofuran and 12.4 g(1.1 mol) of potassium t-butoxide was slowly added thereto. To this solution was slowly added 15.6 g(0.10 mol) of 1-naphthaldehyde dissolved in 20 ml of tetrahydrofuran, then the resulting solution was stirred for 8 hours. The organic solvent was eliminated by distillation under reduced pressure, and the residue was dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate and concentrated. The concentrate was subjected to silica gel column chromatography(eluent: n-hexane/ethyl acetate=95/5, v/v) to obtain 20.3 g(0.090 mol, Yield 90%) of the title compound.

Provenance & Evidence