Potassium Carbonate → 2-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone

HRID 470201노트

반응식

HRID 470201 반응식
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([NH:20][CH2:21][CH:22]=[CH2:23])[CH:18]=[CH2:19]>C(#N)C.C(OCC)(=O)C.O>[CH2:17]([N:20]([CH2:21][CH:22]=[CH2:23])[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4])[CH:18]=[CH2:19]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 597069472-Bromo-1-(5-fluorothiophen-2-yl)ethanone

생성물 1

HCID 866978892-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone수율 87.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 2-bromo-1-(5-fluorothiophen-2-yl)ethanone (13.28 g, 59.53 mmol) in acetonitrile (298 mL) at 0° C. under nitrogen is added potassium carbonate (10.70 g, 77.39 mmol) and diallylamine (9.54 mL, 77.39 mmol). The mixture is allowed to slowly warm to room temperature with stirring over 16 hours then diluted with ethyl acetate (500 mL) and water (200 mL). The phases are separated and the aqueous phase extracted twice with ethyl acetate (100 mL). The combined organic extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with hexanes/ethyl acetate (9:1) to give the title compound (12.45 g, 87%) as a yellow oil. ES/MS (m/e): 240 (M+H).

후처리

  1. customThe phases are separated
  2. extractionthe aqueous phase extracted twice with ethyl acetate (100 mL)
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with hexanes/ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-7bdfcc9ea5cc48ff91db78150a3b7914
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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