Acetic Acid → HCID 53752561, compound

Participants

Reaction Steps

A mixture of 3-Cyclopentyloxy-4-methoxybenzaldehyde (7 g, 31.8 mmol), ethyl acetoacetate (4.13 g, 31.8 mmol), piperidine (275 mg, 3.18 mmol) and glacial acetic acid (100 mg) in toluene (350 ml) was heated at reflux with a Dean-Stark trap for 2 days, during which time, at regular intervals, further additions of piperidine (4×275 mg) and glacial acetic acid (4×100 mg) were made. The reaction mixture was then diluted with water and extracted with methylene chloride (3×150 ml), dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2 ; EtOAc:hexane (1:9)) affordedethyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-2-acetyl-prop-2-enoate (2 g, 19%) as a yellow oil.

Provenance & Evidence