Imidazole → 3-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile

HRID 18399

반응식

HRID 18399 반응식
N1C=CN=C1.CN(C)C=O.[OH:11][CH:12]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:13][C:14]#[N:15].[C:22]([Si:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)Cl)([CH3:25])([CH3:24])[CH3:23]>CCOCC.C(OCC)(=O)C>[O:11]([CH:12]([C:16]1[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=1)[CH2:13][C:14]#[N:15])[Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 219739393-Hydroxy-3-(pyridin-4-yl)propanenitrile

생성물 1

HCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile수율 98.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

Next, imidazole (4.60 g, 67.5 mmol) and N,N-dimethylformamide (30 ml) were added to the obtained 3-hydroxy-3-(4-pyridyl)propionitrile (1.00 g, 6.75 mmol), and the mixture was stirred at room temperature. t-Butyldiphenylchlorosilane (2.23 g, 8.10 mmol) was added to the mixture, and the whole was stirred for one day and then stirred further at an external temperature of 50° C. for three hours. Ethyl acetate (50 ml) and ether (50 ml) were added thereto, and the whole was washed with water (20 ml) three times and saturated brine (30 ml) successively. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile (2.58 g, 98.9%) as a colorless oily matter.

후처리

  1. stirringthe whole was stirred for one day
  2. stirringstirred further at an external temperature of 50° C. for three hours
  3. washthe whole was washed with water (20 ml) three times and saturated brine (30 ml) successively
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1afb9fe9375140518b7d7d258c08a4b4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741346B2

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