Chlorotrimethylsilane → 4-Isobutyl-alpha-trimethylsilyloxystyrene

HRID 1741827Notes

Reaction equation

HRID 1741827 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15]>CN(C)C=O>[CH2:13]([C:17]1[CH:18]=[CH:19][C:20]([C:23]([O:25][Si:2]([CH3:5])([CH3:4])[CH3:3])=[CH2:24])=[CH:21][CH:22]=1)[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 932144'-Isobutylacetophenone

Product 1

HCID 190108494-Isobutyl-alpha-trimethylsilyloxystyreneYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of chlorotrimethylsilane (16.3 g) and triethylamine (30.3 g) in N,N-dimethylformamide (50 ml) was added 4'-isobutylacetophenone (22.0 g). The yellow solid was immediately filtered off, and the filtrate was refluxed for 20 hours. The mixture was cooled, diluted with hexane, and washed with cooled aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated. The residue was distilled under reduced pressure to give 4-isobutyl-α-trimethylsilyloxystyrene (9.0 g) as an oil.

Workup

  1. filtrationThe yellow solid was immediately filtered off
  2. temperaturethe filtrate was refluxed for 20 hours
  3. temperatureThe mixture was cooled
  4. additiondiluted with hexane
  5. washwashed with cooled aqueous sodium bicarbonate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b3101e1ddb20452c9c0bbeb4d6529ea7
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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