Sodium Acetate → 3-Acetoxypropyldimethylvinylsilane

HRID 217566

Reaction equation

HRID 217566 reaction equation
Cl[CH2:2][CH2:3][CH2:4][SiH2:5][CH:6]=[C:7]([CH3:9])[CH3:8].[C:10]([O-:13])(=[O:12])[CH3:11].[Na+]>CN(C=O)C>[C:10]([O:13][CH2:2][CH2:3][CH2:4][SiH2:5][CH:6]=[C:7]([CH3:9])[CH3:8])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 131715857Chloropropyldimethylvinylsilane

Product 1

HCID 1317297653-AcetoxypropyldimethylvinylsilaneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

As shown in the Reaction Scheme 8, a mixture of 3-chloropropyldimethylvinylsilane (1.0 g, 6.15 mmol) and sodium acetate (1.01 g, 12.3 mmol) was dissolved in 17 mL of N,N′-dimethylformamide (DMF), and the resulting solution was heated at 120° C. for 12 hours. After the reaction, the organic layer was extracted with distilled water and ether. After evaporating the solvent, the resulting residue was purified by column chromatography (n-Hex:EA=10:1, Rf=0.36) to give 859 mg (75% yield) of pure 3-acetoxypropyldimethylvinylsilane.

Workup

  1. customAs shown in the Reaction Scheme 8
  2. customAfter the reaction
  3. extractionthe organic layer was extracted with distilled water and ether
  4. customAfter evaporating the solvent
  5. customthe resulting residue was purified by column chromatography (n-Hex:EA=10:1, Rf=0.36)

Sources & evidence

ORD record
ord-20ea7051fb06442c9978dd841d00ada6
Source dataset
uspto-grants-2012_06
Patent number
US08197903B2

Linked notes

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