Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-Biphenyl-4-yl-acrylic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 4-biphenylcarboxaldehyde (7.289 g, 40 mmol) in MeCN (80 ml) under nitrogen at room temperature was added methyl(triphenylphosphoranylidene)acetate (16.049 g, 48 mmol). After 18 h the reaction mixture was concentrated and the residue purified by flash chromatography, eluting with 10% EtOAc/hexane. The appropriate fractions were collected, filtered, concentrated and dried to give 3-biphenyl-4-yl-acrylic acid methyl ester (9.384 g, 39.38 mmol, 98%) as a pale yellow solid, mp 144-147° C. 1H NMR (DMSO-d6) δ 3.75 (s, 3H), 6.70 (d, 1H), 7.35-7.53 (m, 3H), 7.65-7.78 (m, 5H), 7.82 (d, 2H).

Provenance & Evidence