Benzaldehyde → Ethyl Cinnamate

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of lithium tert-butoxide (124.6 g, 1.56 mol, 1.10 equiv) in DCM (2000 mL) under N2 at RT was added ethyl 2-(diethoxyphosphoryl)acetate (317 g, 1.41 mol, 1.00 equiv). Benzaldehyde (150 g, 1.41 mol, 1.0 equiv) was then added dropwise to the stirred reaction, and the resulting reaction mixture was stirred under N2 at 25° C. overnight. The reaction mixture was diluted with DCM (2 L). The organic layer was washed with water (3×2 L) and brine (1×2 L), dried (Na2SO4), filtered, and evaporated in vacuo. The crude residue was purified by SiO2 chromatograph eluting with EtOAc/petroleum ether (3.3 to 1% EtOAc) to afford 180 g (72%) of ethyl (2E)-3-phenylprop-2-enoate (31) as a light yellow oil.

Provenance & Evidence