3-Phenylprop-2-Enal → HCID 86761424, compound

Participants

Reaction Steps

Under argon, 20.9 g (55.4 mmol) of 2-(4-bromophenyl)-4,6-diethoxybenzofuran-3-one are dissolved in 422 ml of degassed methanol and 100 ml of degassed toluene. At RT, 2.00 g (11.1 mmol) of a 30% strength methanolic sodium methoxide solution are added. One minute later, cinnamaldehyde (9.52 g, 72.0 mmol) dissolved in 111 ml of degassed toluene is added. The mixture is stirred at RT overnight and then left to stand for 48 h. Subsequently saturated ammonium chloride solution is added and the mixture is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 10.7 g (38% of theory) of the title compound as racemic mixture and 6.00 g (21% of theory) of the diastereomer (R*,R*)-3-[2-(4-bromophenyl)-4,6-diethoxy-3-oxo-2,3-dihydrobenzofuran-2-yl]-3-phenylpropanal as racemic mixture.

Provenance & Evidence