Sodium Acetate → 3-Acetoxypropyltrivinylsilane

HRID 217567

Reaction equation

HRID 217567 reaction equation
Cl[CH2:2][CH2:3][CH2:4][Si:5]([CH:10]=[CH2:11])([CH:8]=[CH2:9])[CH:6]=[CH2:7].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+]>CN(C)C=O>[C:12]([O:15][CH2:2][CH2:3][CH2:4][Si:5]([CH:10]=[CH2:11])([CH:8]=[CH2:9])[CH:6]=[CH2:7])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 23630656Trivinyl(3-chloropropyl)silane

Product 1

HCID 579455963-AcetoxypropyltrivinylsilaneYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

As shown in Reaction Scheme 24, 3-chloropropyltrivinylsilane (1.0 g, 5.35 mmol) and sodium acetate (0.87 g, 10.7 mmol) were dissolved in 17 mL of dimethylformamide (DMF), and the reaction mixture was heated at 120° C. for 12 hours. After the reaction, the organic layer was separated after addition of distilled water and ether. The organic layer was dried over MgSO4, concentrated by evaporation of solvent, and the resulting residue was purified by column chromatography (n-Hex: EA=10:1, Rf=0.4) to give 855 mg (76% yield) of pure 3-acetoxypropyltrivinylsilane.

Workup

  1. customAfter the reaction
  2. customthe organic layer was separated
  3. additionafter addition of distilled water and ether
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated by evaporation of solvent
  6. customthe resulting residue was purified by column chromatography (n-Hex: EA=10:1, Rf=0.4)

Sources & evidence

ORD record
ord-672dfd5c3911452085a6ee1da2c6cf62
Source dataset
uspto-grants-2012_06
Patent number
US08197903B2

Linked notes

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