1,4-Dichloro-2-(dimethoxymethyl)silyl-2-butene → 2-(Dimethoxymethyl)silyl-1,3-butadiene

HRID 653545Notes

Reaction equation

HRID 653545 reaction equation
Cl[CH2:2][C:3]([SiH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10])=[CH:4][CH2:5]Cl>[Zn].C1COCC1>[CH3:10][O:9][CH:8]([SiH2:7][C:3]([CH:4]=[CH2:5])=[CH2:2])[O:11][CH3:12]

Participants

4

Reactant 1

HCID 1234798241,4-Dichloro-2-(dimethoxymethyl)silyl-2-butene

Product 1

HCID 1236020392-(Dimethoxymethyl)silyl-1,3-butadieneYield 71%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

While 3.5 g (35×1.5 mmols) of Zn powder and 15 ml of THF were agitated, 8.0 g (35 mmols) of 1,4-dichloro-2-(dimethoxymethyl)silyl-2-butene was added. The mixture was heated under reflux for 2 hours, and then treated in the same manner as in Example 1 to obtain 3.9 g of 2-(dimethoxymethyl)silyl-1,3-butadiene.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additiontreated in the same manner as in Example 1

Sources & evidence

ORD record
ord-a75a42add600422d903a9ac76aebcb13
Source dataset
uspto-grants-1987_06
Patent number
US04677216

Reaction notes

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