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

HRID 854669Notes

Reaction equation

HRID 854669 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c0cd53cf70524b15a37a7c5aea8b7a08
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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