Tetrahydrofuran → (Buta-1,3-dien-2-yl)(trimethoxy)silane

HRID 653541Notes

Reaction equation

HRID 653541 reaction equation
C1COCC1.Cl[CH2:7][C:8]([Si:12]([O:17][CH3:18])([O:15][CH3:16])[O:13][CH3:14])=[CH:9][CH2:10]Cl>[Zn].CCCCC>[CH3:14][O:13][Si:12]([O:15][CH3:16])([O:17][CH3:18])[C:8]([CH:9]=[CH2:10])=[CH2:7]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 544102631,4-Dichloro-2-(trimethoxy)silyl-2-butene

Product 1

HCID 13330888(Buta-1,3-dien-2-yl)(trimethoxy)silaneYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8003PentaneSolvent

Procedure

Four grams (41×1.5 mmols) of Zn powder and 15 ml of THF were added, under agitation, to 10 g (41 mmols) of the 1,4-dichloro-2-(trimethoxy)silyl-2-butene obtained by the above procedure. The mixed solution was heated and refluxed for 1 hour and then cooled down to room temperature, followed by adding 30 ml of dried pentane. The resulting ZnCl2 was removed by filtration and the solvent was distilled off under reduced pressure, followed by vacuum distillation to obtain 5.0 g of 2-(trimethoxy) silyl-1,3-butadiene.

Workup

  1. customobtained by the above procedure
  2. temperatureThe mixed solution was heated
  3. temperaturerefluxed for 1 hour
  4. customThe resulting ZnCl2 was removed by filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-b35915a35cb8400f871bf6c3ee681aa5
Source dataset
uspto-grants-1987_06
Patent number
US04677216

Reaction notes

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