Diethyl Oxalate → Ethyl 2,4-dioxoheptanoate

Participants

Reaction Conditions

Reaction Steps

Sodium (11.5 g, 500 mmol) was added to ethanol (130 mL) in portions at room temperature with vigorous stirring. After sodium got dissolved, the solution was cooled to 0° C. Methyl propyl ketone (53.0 mL, 500 mmol) was added dropwise and the stirring was continued for further 15-20 min. Diethyl oxalate (68.0 mL, 500 mmol) was added dropwise to the resulting solution at 0° C. and the stirring was continued for another 15 min at 0° C. The reaction mixture was then allowed to attain room temperature and the stirring was continued for further 12 h at this temperature. The reaction mixture was then kept in refrigerator for 24 h. The solvent was removed under vacuum at room temperature. The resulting residue was diluted with dil. hydrochloric acid on an ice bath and extracted the aqueous layer with diethyl ether (4×50 mL). The combined ether extracts were washed with water, brine, dried (Na2SO4) and concentrated under vacuum. The crude mass was chromatographed on silica gel using 3% ethyl acetate in pet. ether as eluent to yield the title compound (60.0 g, 64.5%).

Provenance & Evidence