Chloromethyl(4-phenylphenyl)divinylsilane → Divinyl(1H-imidazol-1-ylmethyl)(4-phenylphenyl)silane

HRID 371315Notes

Reaction equation

HRID 371315 reaction equation
Cl[CH2:2][Si:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH:6]=[CH2:7])[CH:4]=[CH2:5].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[K]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:4]([Si:3]([CH:6]=[CH2:7])([CH2:2][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[CH2:5]

Participants

5

Reactant 2

HCID 20273719Chloromethyl(4-phenylphenyl)divinylsilaneHCID 67086713Potassium imidazole

Product 1

HCID 13489959Divinyl(1H-imidazol-1-ylmethyl)(4-phenylphenyl)silane

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1.14 g (0.004 mol) of chloromethyl(4-phenylphenyl)divinylsilane in 10 ml of toluene is added 0.54 g (0.005 mol) of potassium imidazole and 0.05 g of tetrabutylammonium bromide. The mixture is refluxed under nitrogen for two days, cooled, diluted with ether-hexanes, and washed with water and brine. Removal of solvent gives an oil which is purified by silica gel chromatography, eluting with 9:1 dichloromethane-ether, to give the title compound.

Workup

  1. temperatureThe mixture is refluxed under nitrogen for two days
  2. temperaturecooled
  3. washwashed with water and brine
  4. customRemoval of solvent
  5. customgives an oil which
  6. customis purified by silica gel chromatography
  7. washeluting with 9:1 dichloromethane-ether

Sources & evidence

ORD record
ord-9f4c7b118be645d997e352a54cb7baa0
Source dataset
uspto-grants-1985_07
Patent number
US04530922

Reaction notes

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