4-Phenoxybutyltriphenylphosphonium bromide → Ethyl (2E)-3-{4-[5-phenoxypent-1-en-1-yl]phenyl}acrylate

Participants

Reaction Conditions

Reaction Steps

3.16 g of (4-phenoxybutyl)(triphenyl)phosphonium bromide are suspended in 25 ml of THF under argon and cooled to −40° C. 2.36 ml of n-butyllithium (1.6 molar in hexane) are added dropwise, and the mixture is warmed to 0° C. after 5 minutes and cooled again to −40° C. after 15 minutes. A solution of 0.70 g of ethyl 4-formylcinnamate in THF is added dropwise and, after 5 minutes, the reaction mixture is warmed to room temperature. The solvent is removed in a rotary evaporator. 0.75 g of product is obtained as an E/Z mixture.

Provenance & Evidence