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

Participants

Reaction Conditions

Reaction Steps

Diethyl carbonate (130 g, 1.1 mol) was dissolved in a suspension of NaH (60% in oil, 50.2 g, 1.3 mol) in anhydrous tetrahydrofuran (1.5 L), and then 1-(4-fluorophenyl)ethanone (150 g, 1.09 mol) was added dropwise at 70° C. The resulting mixture was stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature and poured into HCl (1 N). The mixture was extracted with EtOAc, the organic phase was dried with anhydrous NaSO4 and concentrated in vacuo. The resulting residue was purified using column chromatography (eluted with petroleum ether/EtOAc=50/1) to provide ethyl 3-(4-fluorophenyl)-3-oxopropanoate (217 g, yield: 95%). 1H-NMR (CDCl3, 400 MHz) δ 7.92˜7.97 (m, 2H), 7.07˜7.13 (m, 2H), 4.14˜4.20 (m, 2H), 3.93 (s, 2H), 1.22 (d, J=7.2 Hz, 3H). MS (M+H)+: 211.

Provenance & Evidence