Allyl chloride → (3-Chloropropyl)(triethyl)silane

HRID 65504Notes

Reaction equation

HRID 65504 reaction equation
[SiH:1]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[CH2:8]([Cl:11])[CH:9]=[CH2:10].[SiH](Cl)(Cl)Cl>>[Si:1]([CH2:10][CH2:9][CH2:8][Cl:11])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 7850Allyl chlorideHCID 12052TriethylsilaneHCID 24811Trichlorosilane

Product 1

HCID 12566784(3-Chloropropyl)(triethyl)silaneYield 63%

Procedure

In a 25 ml apparatus, there were combined 11.6 g (0.1 mol) of Et3SiH and 0.05 ml of Pt catalyst solution. Heat was applied to 60° C. and addition of a mixture of 7.7 g (0.1 mol) of allyl chloride and 1.4 g (0.01 mol) of Cl3SiH begun. There was a smooth exothermic reaction up to 80° C. by the end of the addition (15 min) with temperature continuing to rise to 129° C. 5 min later. Vacuum distillation yielded 12.12 g (63.0%) of Et3SiCH2CH2CH2Cl, with a Et3SiCH2CH2CH2Cl/Et3SiCl molar ratio of 2.73. This example shows that low levels of Cl3SiH effectively promote both rate and yield of the reaction between Et3SiH and allyl chloride, particularly when the low levels are maintained throughout the reaction by replenishment.

Workup

  1. temperatureHeat
  2. customwas applied to 60° C.
  3. customa smooth exothermic reaction up to 80° C.
  4. additionby the end of the addition (15 min) with temperature
  5. customto rise to 129° C
  6. custom5 min
  7. distillationVacuum distillation

Sources & evidence

ORD record
ord-e63054bf8700455e8d36e41abd7c4600
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Reaction notes

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