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

HRID 1393163

반응식

HRID 1393163 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 further stirred at an external temperature of 50° C. for three hours. Ethyl acetate (50 ml) and ether (50 ml) were added to the reaction mixture, the whole was washed with water (20 ml) three times and saturated brine (30 ml) successively, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 2.58 g (98.9%) of 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile as a colorless oily matter.

후처리

  1. stirringthe whole was stirred for one day
  2. stirringfurther stirred 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. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-12fafd531f9948ffa0676f271f710eb4
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345064B2

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