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Sodium hydride → (2E)-3-(2-ethyl-2H-indazol-4-yl)acrylonitrile

HRID 1639772
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HRID 1639772 반응식
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH2:14]([N:16]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[CH:25]=O)=[N:17]1)[CH3:15]>O1CCCC1.[Cl-].[NH4+]>[CH2:14]([N:16]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2/[CH:25]=[CH:3]/[C:1]#[N:2])=[N:17]1)[CH3:15]
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 593345522-ethyl-2H-indazole-4-carbaldehyde

생성물 1

HCID 59334569(2E)-3-(2-ethyl-2H-indazol-4-yl)acrylonitrile수율 93.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 25517
Ammonium Chloride
용매

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온도
0 °C

실험 절차

To a solution of diethyl cyanomethylphosphonate (254 μL, 1.57 mmol) in tetrahydrofuran (6 mL) was added 60% sodium hydride (57.9 mg, 1.45 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 15 min. To the mixture was added a solution of 2-ethyl-2H-indazole-4-carbaldehyde (210 mg, 1.20 mmol) in tetrahydrofuran (6 mL) under ice-cooling, and the mixture was stirred under ice-cooling for 15 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→50/50) to give the title compound (222 mg, yield 93%).

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 15 min
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→50/50)

출처 및 근거

ORD 기록
ord-bcbade188e9f45198606bf614c8ae2bf
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08110585B2

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