Diethyl Oxalate → 2,4-Dioxo-5-phenoxy-hexanoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Sodium (82 mg, 3.55 mmol) was added to EtOH absolute (9.8 mL) at 0° C. The mixture was stirred at 0° C. until the sodium was completely dissolved. Then (rac)-3-phenoxy-butan-2-one (530 mg, 3.23 mmol) was added dropwise. The mixture was stirred at 0° C. for 10 minutes. Then diethyl oxalate (0.44 mL, 3.23 mmol) was added. Then the mixture was stirred at room temperature for 16 hours and the solvent evaporated in vacuo. The residue was diluted with water, the mixture acidified with a 1M solution of HCl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by open column chromatography (silica; DCM 100%) to yield (rac)-2,4-dioxo-5-phenoxy-hexanoic acid ethyl ester (566 mg, 58% yield) as an orange oil.

Provenance & Evidence