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

HRID 1393163

Reaktionsgleichung

Reaktionsgleichung von HRID 1393163
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrileAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-12fafd531f9948ffa0676f271f710eb4
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345064B2

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