Methyl Acrylate → Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

Provenance & Evidence