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

HRID 65505Notes

Reaction equation

HRID 65505 reaction equation
[SiH:1]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[SiH](Cl)(Cl)Cl.[CH2:12]([Cl:15])[CH:13]=[CH2:14]>>[Si:1]([CH2:14][CH2:13][CH2:12][Cl:15])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 7850Allyl chloride2×HCID 12052TriethylsilaneHCID 24811Trichlorosilane

Product 1

HCID 12566784(3-Chloropropyl)(triethyl)silaneYield 40.9%

Conditions

Temperature
65 °C

Procedure

In a 100 ml apparatus, there were combined 11.6 g (0.1 mol) of Et3SiH, 1.7 g (0.0125 mol) of Cl3SiH and 0.05 ml of Pt catalyst solution. The mixture was heated to 65° C. and addition of 7.7 g (0.1 mol) of allyl chloride begun. There was an exothermic reaction to 108.5° C. over 16 min, followed by a temperature drop. Addition of allyl chloride was complete in 31 min, with heat then applied at reflux (up to 114° C.) over 170 min. Vacuum distillation yielded 7.88 g (40.9%) of Et3SiCH2CH2CH2Cl with a Et3SiCH2CH2CH2Cl/Et3SiCl selectivity ratio of 1.13. This example shows that this sequence of combination of reactants allows the Cl3SiH promoter to be consumed, at which point the reaction of Et3SiH with allyl chloride proceeds at the low rate and selectivity exhibited in Comparative Example DD.

Workup

  1. customan exothermic reaction to 108.5° C. over 16 min
  2. temperaturewith heat
  3. temperatureat reflux (up to 114° C.) over 170 min
  4. distillationVacuum distillation

Sources & evidence

ORD record
ord-4de9006738214215a53917a7083e555b
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Reaction notes

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