Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 4-(4-chlorophenyl)-2-pentenoate

Participants

Reaction Steps

To a stirred solution of 3.9 g (0.023 mole) of 2-(4-chlorophenyl)propionaldehyde in 25 mL of 1,4-dioxane is added in one portion 9.0 g (0.026 mole) of (carbethoxymethylene)triphenylphosphorane. The reaction mixture is stirred for approximately 16 hours at ambient temperature after which the solvent is evaporated under reduced pressure, leaving a residue which is then dissolved in ethyl acetate. Approximately 10 g of silica gel is mixed with the resulting solution. The solvent is evaporated from this mixture, and the residue is placed in a sintered glass filter. The silica gel is then eluted with 100 mL of heptane/ethyl acetate (3:1). These solvents are evaporated under reduced pressure, leaving a residue. This residue is dissolved in 30 mL of heptane/ethyl acetate (9:1), treated with 5 g of silica gel, and filtered. The filtrate is evaporated under reduced pressure, leaving ethyl 4-(4-chlorophenyl)-2-pentenoate as a residue.

Provenance & Evidence