3-Chloro-2-methyl-1-propene → Chlorotriethylsilane

HRID 65496

Reaction equation

HRID 65496 reaction equation
[SiH:1]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[CH2:8]([Cl:12])[C:9](=[CH2:11])[CH3:10]>>[Si:1]([Cl:12])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[Si:1]([CH2:10][CH:9]([CH2:8][Cl:12])[CH3:11])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 112413-Chloro-2-methyl-1-propeneHCID 12052Triethylsilane

Product 2

HCID 13819ChlorotriethylsilaneYield 36.8%HCID 13765477Et3SiCH2CHMeCH2ClYield 18.7%

Conditions

Temperature
115 °C

Procedure

A mixture of Et3SiH (10.5 g, 0.09 mol) and methallyl chloride (8.2 g, 0.09 mol) was combined in a 150 ml apparatus and 0.05 ml Pt catalyst solution added, followed by heating at reflux (115° C.) for 50 hr. Additional Pt catalyst solution (0.025 ml) was added at 40 hr. The incomplete reaction was distilled, yielding 4.98 g (36.8%) of Et3SiCl and 3.48 g (18.7%) of Et3SiCH2CHMeCH2Cl. This example shows that the unpromoted reaction of Et3SiH with methallyl chloride is very slow and endothermic.

Workup

  1. additionadded
  2. temperatureby heating
  3. customThe incomplete reaction
  4. distillationwas distilled

Sources & evidence

ORD record
ord-8b9e62e66c254e3f9fb282c319c0df4f
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Linked notes

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