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

HRID 18399

Reaction equation

HRID 18399 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1afb9fe9375140518b7d7d258c08a4b4
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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