Hydrochloric Acid → Ethyl 3-(2-fluorophenyl)-3-oxopropanoate

To a solution of 2-fluorobenzoic acid (25.3 g, 181 mmol) in tetrahydrofuran (300 ml) was added 1,1′-carbonylbis-1H-imidazole (32.2 g, 198 mmol) and the mixture was stirred at room temperature for 30 min. To the reaction solution was added monoethyl malonate magnesium salt (27.1 g, 94.7 mmol) and the mixture was heated under reflux for 30 min. Ethyl acetate (50 ml) and water (50 ml) were added to the reaction solution, and conc. hydrochloric acid was added until the aqueous layer showed acidic pH. The reaction solution was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-(2-fluorophenyl)-3-oxopropionate (31.9 g, 84%) as a colorless oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 30 min
3. additionwas added until the aqueous layer
4. extractionThe reaction solution was extracted with ethyl acetate (200 ml×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

ORD 기록

ord-9e841364890b48a89b16d06241218d1a

출처 데이터셋

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06982348B2