Imidazole → 3-((tert-Butyldimethylsilyl)oxy)propanenitrile

HRID 1427657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427657
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][CH2:16][C:17]#[N:18]>CN(C=O)C>[Si:6]([O:14][CH2:15][CH2:16][C:17]#[N:18])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 8011HydracrylonitrileHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 105355293-((tert-Butyldimethylsilyl)oxy)propanenitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (33.6 g, 495 mmol) and tert-butyldimethylsilyl chloride (27.2 g, 180 mmol) were added to a 0° C. solution of 3-hydroxypropanenitrile (10.6 g, 150 mmol) in DMF 50 mL). The mixture was allowed to warm to rt, then was stirred at rt for 12 hrs. The mixture was quenched with water (500 mL), and then extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (gradient elution 0-5% EtOAc/petroleum ether) to give 3-(tert-butyldimethylsilyloxy) propanenitrile (18 g, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.74 (t, J=6.0 Hz, 2H), 2.43 (t, J=6.0 Hz, 2H), 0.81 (s, 9H), 0.00 (s, 6H).

Aufarbeitung

  1. customThe mixture was quenched with water (500 mL)
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (gradient elution 0-5% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-851513abfe48454a87635460c7e542a5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933233B2

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