Acetic Acid → HCID 367495, compound

Participants

Reaction Steps

Piperidine (4.0 mL) and glacial acetic acid (12 mL) were added to a stirred solution of ethyl acetoacetate (127.5 mL, 1.0 mol) and 4-fluorobenzaldehyde (136.52 g, 1.1 mol) in 200 mL of toluene. This mixture was heated under reflux for four hours with azeotropic removal of water. The reaction mixture was cooled to room temperature and concentrated. The residue was flash chromatographed on silica gel, eluting with toluene, to produce 226.0 g of crude product which was then distilled to yield 186.2 g of a mixture of cis- and trans-ethyl 2-[(4-fluorophenyl)methylene]-3-oxobutanoate, bp 160°-170° C. at 5 mm Hg.

Provenance & Evidence