Carbon Tetrachloride → 2-(4-Ethoxyphenyl)-2-methyl-2-silapropyl acetate

HRID 1639231Notes

Reaction equation

HRID 1639231 reaction equation
Cl[CH2:2][Si:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[C:15]([O-:18])(=[O:17])[CH3:16].[Na+].C(Cl)(Cl)(Cl)Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[C:15]([O:18][CH2:2][Si:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 184717Silane, (chloromethyl)(4-ethoxyphenyl)dimethyl-HCID 517045Sodium Acetate2×

Product 1

HCID 140144832-(4-Ethoxyphenyl)-2-methyl-2-silapropyl acetateYield 105.4%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

In a flask under nitrogen were placed 10.1 g (0.044 mole) of (chloromethyl)(4-ethoxyphenyl)dimethylsilane, 4.0 g (0.049 mole) of sodium acetate, 1.2 g (0.0043 mole) of tetrabutylammonium chloride, and 75 mL of carbon tetrachloride. This mixture was refluxed for four days. After cooling to room temperature, 2.0 g (0.024 mole) of sodium acetate and 0.60 g (0.0022 mole) of tetrabutylammonium chloride was added, and the reaction mixture was refluxed for five more days. This mixture was then diluted with diethyl ether, filtered through silica gel, and the solvent was evaporated under reduced pressure, leaving 11.7 g of 2-(4-ethoxyphenyl)-2-methyl-2-silapropyl acetate as a clear, light brown oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask under nitrogen were placed
  2. temperatureThis mixture was refluxed for four days
  3. temperaturethe reaction mixture was refluxed for five more days
  4. filtrationfiltered through silica gel
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bde9df51825340e5aa6f28549b254119
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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