Imidazole → (cis-3-Allylcyclohexyloxy)-tert-butyldiphenylsilane

HRID 854669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854669
[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([OH:10])[CH2:5]1)[CH:2]=[CH2:3].[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CN=C1.CC1C=CN=C(N)C=1C>CN(C)C=O.C(OC)(C)(C)C>[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5]1)[CH:2]=[CH2:3]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 110078842-Amino-3,4-dimethylpyridineHCID 58763359cis-3-Allylcyclohexanol

Produkt 1

HCID 69242153(cis-3-Allylcyclohexyloxy)-tert-butyldiphenylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

6.8 g of cis-3-allylcyclohexanol are, together with 15 ml of tert-butyl-diphenylsilyl chloride, 5 g of imidazole and 200 mg of dimethyl-aminopyridine, dissolved in 100 ml of dimethylformamide, and the mixture is stirred at room temperature for 12 h. 400 ml of methyl tert-butyl ether are added to the reaction mixture, and the mixture is washed three times with water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. This gives 20.5 g of (cis-3-allylcyclohexyloxy)-tert-butyl-diphenyl-silane as an oil. C25H340Si (378.64), MS(ESI): 379 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.93.

Aufarbeitung

  1. washthe mixture is washed three times with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c0cd53cf70524b15a37a7c5aea8b7a08
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259177B2

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