Hydrochloric Acid → methyl (2-oxopropoxy)acetate

Participants

Reaction Conditions

Reaction Steps

2M Dimethyl zinc in toluene (21 mL, 42 mmol) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (0.57 g, 76 mmol) were treated with methyl 2-(chloroformylmethoxy)acetate (12.6 g, 76 mmol) dropwise over 0.5 hours at 0° C. under a nitrogen atmosphere. After stirring for 0.5 hours at 0° C., the mixture was allowed to warm to ambient temperature and stir for 16 hours. The reaction mixture was treated with 1 M HCl (40 mL) and brine (20 mL). The phases were separated and the organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (1:2 ethyl acetate:hexanes) to provide the title compound (5.2 g).

Provenance & Evidence