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

HRID 1792408노트

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HRID 1792408 반응식
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[F:17][C:18]([F:28])([C:24]([F:27])([F:26])[F:25])[CH2:19][CH2:20][C:21](Cl)=[O:22]>C1COCC1>[F:17][C:18]([F:28])([C:24]([F:25])([F:26])[F:27])[CH2:19][CH2:20][C:21](=[O:22])[CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 220330904,4,5,5,5-Pentafluoropentanoyl chloride

생성물 1

HCID 22033121Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c9a8b8dff5a04d489160160a139b1a41
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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