3-Chloro-1-butene → Chlorotriethylsilane

HRID 65510

Reaction equation

HRID 65510 reaction equation
[SiH:1]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[Cl:8][CH:9]([CH3:12])[CH:10]=[CH2:11]>>[Si:1]([Cl:8])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3].[Si:1]([CH2:11][CH2:10][CH:9]([Cl:8])[CH3:12])([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 112423-Chloro-1-buteneHCID 12052Triethylsilane

Product 2

HCID 13819ChlorotriethylsilaneYield 58.9%HCID 13765479Et3SiCH2CH2CHMeClYield 7.6%

Conditions

Temperature
77 °C

Procedure

In a 50 ml apparatus, there were combined 4.5 g (0.039 mol) of Et3SiH and 3.5 g (0.039 mol) of 3-chloro-1-butene. Pt catalyst solution (0.01 ml) was added at 22° C., followed by heating up to 77° C. over 70 min. Vacuum distillation yielded 3.46 g (58.9%) of Et3SiCl and 0.61 g (7.6%) of Et3SiCH2CH2CHMeCl. This example demonstrates the low yield of Et3SiCH2CH2CHMeCl from the unpromoted reaction of Et3SiH with 3-chloro-1-butene.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-45673193f8e042e78e06b4e60f4b1eb9
Source dataset
uspto-grants-1986_09
Patent number
US04614812

Linked notes

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