Acetic Acid → HCID 69734031, compound

Participants

Reaction Steps

A solution of ethyl 3-ketohexanoate (6.6 g), 1-naphthaldehyde (7.34 g), piperidine (1.2 g) and acetic acid (2.25 g) in benzene (50 mL) was heated under reflux for 3 hours and the reaction mixture was dehydrated using a Dean-Stark condenser. The solvent was evaporated and the residue was purified by silica gel column chromatography using an eluent (hexane-ethyl acetate (3:1)) to give ethyl 2-(naphthalen-1-yl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture) as a yellow oil. The title compound was obtained as a colorless amorphous solid from ethyl 2-(naphthalen-1-yl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture), 3-amino-2-methylpyrazole and p-toluenesulfonic acid.

Provenance & Evidence