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

HRID 65506Notes

Reaction equation

HRID 65506 reaction equation
[CH2:1]([Cl:4])[CH:2]=[CH2:3].[SiH:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].[SiH](Cl)(Cl)Cl>>[Si:5]([CH2:3][CH2:2][CH2:1][Cl:4])([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 7850Allyl chlorideHCID 12052TriethylsilaneHCID 24811Trichlorosilane

Product 1

HCID 12566784(3-Chloropropyl)(triethyl)silaneYield 40.5%

Conditions

Temperature
44 °C

Procedure

In a 50 ml apparatus, there were combined 7.7 g (0.1 mol) of allyl chloride and 0.05 ml of Pt catalyst solution. the mixture was heated to 44° C. and addition of a mixture of 11.6 g (0.1 mol) of Et3SiH and 1.4 g (0.01 mol) of Cl3SiH begun. Reaction was heated up to 54.5° C. during addition (30 min). There was a violent exothermic reaction from 62° C. to 110° C. 16 min later. Vacuum distillation yielded 7.79 g (40.5%) of Et3SiCH2CH2CH2Cl, with a Et3SiCH2CH2CH2Cl/Et3SiCl selectivity ratio of 1.23. This example and the previous one show that the preferred sequence of combination of reactants for most effective Cl3SiH promotion of the reaction of Et3SiH with allyl chloride is that of Example 24.

Workup

  1. customReaction
  2. temperaturewas heated up to 54.5° C. during addition (30 min)
  3. customa violent exothermic reaction from 62° C. to 110° C
  4. custom16 min
  5. distillationVacuum distillation

Sources & evidence

ORD record
ord-5761f7db8f3a4ee096a35db6e70f0979
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Reaction notes

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