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 acetonitrile and 30.4 g(0.2 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5)(DBU) 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 and the mixture was stirred for 8 hours. The organic solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate, concentrated and then 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