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

HRID 653542Notes

Reaction equation

HRID 653542 reaction equation
Cl[Si:2](Cl)(Cl)[C:3]([CH:5]=[CH2:6])=[CH2:4].C1[CH2:13][O:12]CC1.[CH3:14][OH:15].CC[O:18][CH2:19]C>N(CC)(CC)CC>[CH3:14][O:15][Si:2]([O:12][CH3:13])([O:18][CH3:19])[C:3]([CH:5]=[CH2:6])=[CH2:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 133308912-Trichlorosilyl-1,3-butadiene

Product 1

HCID 13330888(Buta-1,3-dien-2-yl)(trimethoxy)silaneYield 75%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Conditions

Temperature
-10 °C

Procedure

A mixture of 8.7 g (46 mmols of crude product) of 2-(trichloro)silyl-1,3-butadiene and 10 ml of THF was cooled down to -10° C., into which was gently dropped a mixture of 8.3 ml (46×31.5 mmols) of CH3OH and 28.9 ml (46×3×1.5 mmols) of (C2H5)3N while agitating. Thereafter, the mixture was agitated at room temperature for further 30 minutes, followed by adding 30 ml of (C2H5)2O. The resulting (C2H5)3N.HCl was removed by filtration and the solvent was distilled off under reduced pressure, followed by vacuum distillation to obtain 6.1 g of 2-(trimethoxy)silyl-1,3-butadiene. Yield: 75%.

Workup

  1. additionwas gently dropped
  2. stirringThereafter, the mixture was agitated at room temperature for further 30 minutes
  3. customThe resulting (C2H5)3N.HCl was removed by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-ee7f42dd792843cc9dc4ab28731ac5e0
Source dataset
uspto-grants-1987_06
Patent number
US04677216

Reaction notes

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