Imidazole → (4-Ethenylphenoxy)tri(propan-2-yl)silane

HRID 1795308Notes

Reaction equation

HRID 1795308 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2].N1C=CN=C1.[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].O>CN(C)C=O>[CH:15]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 624534-VinylphenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 22186413(4-Ethenylphenoxy)tri(propan-2-yl)silaneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 300 ml glass-made three-neck flask was charged with 0.134 mol of p-vinylphenol, 0.343 mol of imidazole and 90 ml of dimethylformamide as a solvent, and a solution prepared by dissolving 0.174 mol of triisopropylsilyl chloride in 90 ml of dimethylformamide was dropwise added thereto at 0° C. in 50 minutes. Then, the reaction temperature was elevated up to room temperature to carry out reaction for 10 hours in the same condition. Water was added thereto, and the reaction product was extracted with chloroform. The solvent was distilled off, and the residue was dissolved in diethyl ether and washed with a sodium hydroxide aqueous solution and water. The product was dried on magnesium sulfate and filtered, and then it was further dried on a calcium hydride. Then, the reaction product was distilled at a reduced pressure under nitrogen flow to obtain aimed p-triisopropylsilyloxystyrene at a yield of 70%.

Workup

  1. customa solution prepared
  2. additionwas dropwise added
  3. customwas elevated up to room temperature
  4. customreaction for 10 hours in the same condition
  5. extractionthe reaction product was extracted with chloroform
  6. distillationThe solvent was distilled off
  7. dissolutionthe residue was dissolved in diethyl ether
  8. washwashed with a sodium hydroxide aqueous solution and water
  9. customThe product was dried on magnesium sulfate
  10. filtrationfiltered
  11. dry with materialit was further dried on a calcium hydride
  12. distillationThen, the reaction product was distilled at a reduced pressure under nitrogen flow

Sources & evidence

ORD record
ord-72d74a427fd1444794abccae80713866
Source dataset
uspto-grants-2006_04
Patent number
US07026406B1

Reaction notes

Loading…