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

HRID 347413Notes

Reaction equation

HRID 347413 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.CN(C1C=CC=CN=1)C>CN(C)C=O>[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

6

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 58763359cis-3-Allylcyclohexanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.8 g of cis-3-allylcyclohexanol and 15 ml of tert-butyldiphenylsilyl chloride, 5 g of imidazole and 200 mg of dimethylaminopyridine are dissolved in 100 ml of dimethylformamide and stirred at room temperature for 12 hours. 400 ml of methyl tert-buthyl ether are added to the reaction mixture, and the mixture is washed three times with water. The organic phase is dried over magnesium sulfate and the solvent is then removed under reduced pressure. This gives 20.5 g of (cis-3-allylcyclohexyloxy)tert-butyl-diphenylsilane as an oil. C25H34OSi (378.64), MS(ESI): 379 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.93.

Workup

  1. addition400 ml of methyl tert-buthyl ether are added to the reaction mixture
  2. washthe mixture is washed three times with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-0dd4868422534308b9e7e52c70105a0b
Source dataset
uspto-grants-2007_02
Patent number
US07173151B2

Reaction notes

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