Acetic Acid → Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Participants

Reaction Steps

To a suspension of diethyl carbonate (47.4 mL, 391 mmol) and sodium hydride (55 wt % paraffin oil, 23.7 g, 543 mmol) in THF was added 4′-fluoroacetophenone (26.4 mL, 271 mmol) at 60° C. The reaction mixture was heated under reflux for 1 hr, cooled to room temperature, and poured into acetic acid (33.6 ml, 586 mmol) and ice water (1 L). The reaction mixture was extracted with diethyl ether (2×500 mL), the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure to give ethyl 3-(4-fluorophenyl)-3-oxopropanoate (45.7 g, 100%, keto form: enol for m=5:1) as a yellow oil.

Provenance & Evidence