Allyl chloride → 3-(Trimethoxysilyl)propyl chloride

HRID 985734Notes

Reaction equation

C(Cl)C=C.C(O[SiH](OCC)OCC)C.[Cl:15][CH2:16][CH2:17][CH2:18][Si:19]([O:26][CH2:27]C)([O:23][CH2:24]C)[O:20][CH2:21]C.CO[SiH](OC)OC>>[Cl:15][CH2:16][CH2:17][CH2:18][Si:19]([O:26][CH3:27])([O:20][CH3:21])[O:23][CH3:24]

Participants

Reactant 4

HCID 7850Allyl chloride3×

HCID 13830Triethoxysilane

HCID 17215Trimethoxysilane

HCID 78771(3-Chloropropyl)triethoxysilane

Product 1

HCID 624493-(Trimethoxysilyl)propyl chlorideYield 70%

Procedure

A potentially more economical route is the direct hydrosilation reaction of triethoxysilane and allyl chloride. Platinum is the most widely used hydrosilation catalyst and its use for the hydrosilation reaction of allyl chloride and triethoxysilane has been reported. According to U.S. Pat. No. 3,795,656, a 70% yield was obtained for the Pt-catalyzed hydrosilation reaction of allyl chloride and triethoxysilane. Belyakova et al., Obshch. Khim 1974, 44, 2439-2442, describes the Pt-catalyzed hydrosilation reaction of silanes with allyl chloride and reports a 14% yield for chloropropyltriethoxysilane. As disclosed in Japanese Patent No. 11,199,588, the Pt-catalyzed hydrosilation reaction of trimethoxysilane and allyl chloride resulted in a 70% yield of chloropropyltrimethoxysilane.

Sources & evidence

ORD record: ord-82ddf3d75de9436bbf91c2982b28985a
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872845B2

Reaction notes

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