Allyl chloride → Chlorotriethylsilane

HRID 65503

Reaction equation

HRID 65503 reaction equation
[SiH:1]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[CH2:8]([Cl:11])[CH:9]=[CH2:10]>>[Si:1]([Cl:11])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[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 2

HCID 7850Allyl chlorideHCID 12052Triethylsilane

Product 2

HCID 13819ChlorotriethylsilaneYield 42%HCID 12566784(3-Chloropropyl)(triethyl)silaneYield 15.5%

Conditions

Temperature
27 °C

Procedure

In a 100 ml apparatus, there were combined 11.6 g (0.1 mol) of Et3SiH, 7.7 g (0.1 mol of allyl chloride, and 0.05 ml Pt catalyst solution at 19° C. After stirring 1 hr, temperature had increased to 27° C., followed by heating at 70° C. for 17 hr. The incomplete reaction was vacuum distilled, yielding 8.9 g (42%) of Et3SiCl, and 3.0 g (15.5%) of Et3SiCH2CH2CH2Cl. The Et3SiCH2CH2C2Cl/Et3SiCl molar selectivity ratio was 0.37. This example shows that the unpromoted reaction between Et3SiH and CH2 =CHCH2Cl is very slow.

Workup

  1. customat 19° C
  2. temperatureby heating at 70° C. for 17 hr
  3. customThe incomplete reaction
  4. distillationdistilled

Sources & evidence

ORD record
ord-e30a5601495043339abb7adf624c51b0
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Linked notes

Loading…