Imidazole → Tert-butyl-(cyclohept-4-enyloxy)-diphenyl-silane

HRID 16226

Reaktionsgleichung

Reaktionsgleichung von HRID 16226
[CH:1]1([OH:8])[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([Si:18]([O:8][CH:1]1[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 556485Cyclohept-4-enol

Produkt 1

HCID 67512396Tert-butyl-(cyclohept-4-enyloxy)-diphenyl-silane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the product of Example 8B (1.57 g, 14.05 mmoles), imidazole (1.43 g, 21.08 mmoles), and Tert-butyl-chlorodiphenylsilane (4.76 gm, 17.4 mmoles) in N,N-dimethylformamide (10 mL) was stirred for five hours at 23° C. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine (25 mL), dried with MgSO4, filtered, and solvent evaporated in vacuo. The crude product was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 90:10) to provide the title compound as an oil.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine (25 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-84851ac9e32e4a5d977463b84fec4a0b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737137B2

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