Diethoxydimethylsilane → Allylethoxyldimethylsilane

HRID 1353024Notes

Reaction equation

HRID 1353024 reaction equation
O([Si:4]([O:7][CH2:8][CH3:9])([CH3:6])[CH3:5])CC.[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>CCOCC>[CH2:12]([CH2:9][CH2:8][O:7][SiH:4]([CH3:5])[CH3:6])[CH:11]=[CH2:10]

Participants

4

Reactant 2

HCID 62322DiethoxydimethylsilaneHCID 178455850HCID 178455850, compound

Product 1

HCID 123297224AllylethoxyldimethylsilaneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

In a 1000 ml flame-dried flask equipped with a magnetic stir bar, 250 ml of dry ether and 37 g (250 mmol) of diethoxyldimethylsilane were injected under argon. The solution was vigorously stirred while 250 ml of allylmagnesiumbromide in ether (1.0 M) was added dropewise over 2 hours. The solution was refluxed overnight to complete the coupling reaction. After cooling the mixture to −20° C. and removing the solid by filtration, the solvent was removed by rovaperation. The raw product was subjected to vacuum distillation to obtain 30 g of pure allylethoxyldimethylsilane (colorless liquid) with yield of 84%.

Workup

  1. customIn a 1000 ml flame-dried flask
  2. customequipped with a magnetic stir bar
  3. additionwas added dropewise over 2 hours
  4. temperatureThe solution was refluxed overnight
  5. customthe coupling reaction
  6. customremoving the solid
  7. filtrationby filtration
  8. customthe solvent was removed by rovaperation
  9. distillationThe raw product was subjected to vacuum distillation

Sources & evidence

ORD record
ord-28851eed47bb49a1bec13ee3b443d7a3
Source dataset
uspto-grants-2007_05
Patent number
US07220807B2

Reaction notes

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