2-(Bromomethyl)acrylic acid ethyl ester → HCID 68308792, compound

Participants

Reaction Steps

To a mixture of ethyl 2-(bromomethyl)acrylate (20.42 g) and toluene (320 mL) was added dropwise a mixture of a 40% methylamine-methanol solution (240.1 mL) and toluene (80 mL) under ice cooling while stirring. The mixture was stirred for 3 minutes. To the mixture was added a mixture of 1,4-cyclohexandione monoethylene ketal (14.00 g) and toluene (100 mL) under the same conditions. The mixture was refluxed with the Dean-Stark apparatus for 4.5 hours. After cooling to room temperature, the mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-40% ethyl acetate/hexane, gradient elution) to give the title compound (22.92 g).

Provenance & Evidence