Triethylamine → HCID 60018558, compound

HRID 896951Notes

Reaction equation

HRID 896951 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[CH:23]([Si:25]([O:30][CH3:31])([O:28][CH3:29])[O:26][CH3:27])=[CH2:24]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH3:27][O:26][Si:25]([O:30][CH3:31])([O:28][CH3:29])[CH:23]=[CH:24][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76004VinyltrimethoxysilaneHCID 22345880HCID 22345880, compound

Product 1

HCID 60018558HCID 60018558, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Into a mixture of 20 ml of triethylamine and 40 ml of acetonitrile, were dissolved 15.0 g (54.9 mmol) of 1-(t-butoxycarbonyloxy)-4-bromobenzene synthesized in the step (i) and 9.76 g (65.9 mmol) of vinyltrimethoxysilane, and the reaction system was substituted by argon by bubbling argon in thus obtained solution. In the reaction system, was added 246.5 mg (1.1 mmol) of palladium acetate as a catalyst, the mixture was refluxed for one night. After completion of the reaction, solvent was removed, and the obtained residue was extracted by hexane. Hexane was removed from the extraction to prepare 9.5 g of 1-(2-trimethoxysilylvinyl)-4-(t-butoxycarbonyloxy)benzene being the objective compound.

Workup

  1. customby bubbling argon in thus obtained solution
  2. temperaturethe mixture was refluxed for one night
  3. customAfter completion of the reaction, solvent
  4. customwas removed
  5. extractionthe obtained residue was extracted by hexane
  6. customHexane was removed from the extraction
  7. customto prepare 9.5 g of 1-(2-trimethoxysilylvinyl)-4-(t-butoxycarbonyloxy)benzene being the objective compound

Sources & evidence

ORD record
ord-bd74887f691342d382adc5daea6c34c7
Source dataset
uspto-grants-2005_07
Patent number
US06921623B2

Reaction notes

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