Allyl chloride → Silane, chloro(3-chloropropyl)dimethyl-

HRID 65507

Reaction equation

HRID 65507 reaction equation
[SiH:1]([Cl:4])([CH3:3])[CH3:2].[SiH:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].[CH2:12]([Cl:15])[CH:13]=[CH2:14]>>[Si:1]([CH2:14][CH2:13][CH2:12][Cl:15])([CH3:3])([CH3:2])[Cl:4].[Si:5]([CH2:14][CH2:13][CH2:12][Cl:15])([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 12052TriethylsilaneHCID 66108Chlorodimethylsilane

Product 2

HCID 82765Silane, chloro(3-chloropropyl)dimethyl-Yield 42.5%HCID 12566784(3-Chloropropyl)(triethyl)silaneYield 4.8%

Procedure

In a 100 ml apparatus, there were combined 7.1 g (0.075 mol) of Me2SiHCl, 8.7 g (0.075 mol) of Et3SiH and 5.7 g (0.075 mol) of allyl chloride. Pt catalyst solution was added (0.05 ml) at 34° C. Gentle heating caused a smooth exothermic reaction to 92° over 36 min. Vacuum distillation yielded 42.5% of Me2SiClCH2CH2CH2Cl and 4.8% of Et3SiCH2CH2CH2Cl. This example shows that Et3SiH at the equimolar level is an effective promoter for the reaction between Me2SiHCl and allyl chloride.

Workup

  1. additionPt catalyst solution was added (0.05 ml) at 34° C
  2. temperatureGentle heating
  3. customa smooth exothermic reaction to 92° over 36 min
  4. distillationVacuum distillation

Sources & evidence

ORD record
ord-ea010ac8c17a469998fda743e4cb84e6
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Linked notes

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