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Ethyl Acetate → 3-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamine

HRID 18400
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인쇄 미리보기

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HRID 18400 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][C:27]#[N:28])[Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)C.O>[Si:8]([O:7][CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][CH2:27][NH2:28])([C:21]([CH3:23])([CH3:24])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile

생성물 1

HCID 121366443-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamine

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 3283Diethyl Ether용매2회

실험 절차

Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, a solution of the obtained 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile (1.00 g, 2.59 mmol) in anhydrous diethyl ether (15 ml) was added dropwise to the suspension under ice-cooling with stirring over eight minutes, and the mixture was stirred at room temperature for 75 minutes. Ethyl acetate (15 ml) was added to the reaction mixture under ice-cooling, water (0.28 ml), a 15% aqueous sodium hydroxide solution (0.28 ml) and water (0.85 ml) were added thereto successively, and the whole was stirred at room temperature for 10 minutes. The reaction mixture was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (180.0 mg, yellow oily matter, 17.8%).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 75 minutes
  3. temperaturecooling
  4. stirringsuccessively, and the whole was stirred at room temperature for 10 minutes
  5. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customto give the target compound (180.0 mg, yellow oily matter, 17.8%)

출처 및 근거

ORD 기록
ord-e1396d93e9d0446f8ff1ba7a7f83be1d
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741346B2

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