Ethyl 4-bromo-3-oxobutanoate → Ethyl 4-hydroxy-3-oxobutanoate

Participants

Reaction Steps

To a solution of 4-bromo-3-ketobutyric acid ethyl ester (2a) (21 g, 0.10 moles) in methanol dried prior to use with Molecular Sieves is added sodium formate (10.2 g, 0.15 moles), and the mixture is refluxed for 1 hour. The reaction mixture is concentrated under reduced pressure to remove the solvent. The residue is extracted with chloroform. The extract is purified by silica gel column chromatography (eluting solvent=benzene/ethyl acetate (2:1)) to give the title compound (3a). Yield: 7.34 g, 50%.

Provenance & Evidence