Ethyl Acetate → Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate

To a stirred solution of ethyl acetate enolate, prepared from ethyl acetate (4.4 g, 50 mmol) and sodium hexamethyldisilazide (50 mmol) in THF at −70° C., was added neat 4,4,5,5,5-pentafluoropentanoyl chloride (2.1 g, 10 mmol) at −70° C. Cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The mixture was diluted with diethyl ether and quenched with water. The organic layer was separated, washed with aqueous 2 N hydrochloric acid, saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuum. The crude product was purified by flash chromatography on-silica gel (hexane ethyl acetate 5:1) to give ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate as colorless oil yield: 1.46 g (56%).

1. temperatureCooling bath
2. customwas removed
3. additionThe mixture was diluted with diethyl ether
4. customquenched with water
5. customThe organic layer was separated
6. washwashed with aqueous 2 N hydrochloric acid, saturated sodium bicarbonate solution, brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated in vacuum
9. customThe crude product was purified by flash chromatography on-silica gel (hexane ethyl acetate 5:1)

ORD record

ord-c9a8b8dff5a04d489160160a139b1a41

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074819B2