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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 402920Generated: October 30, 2026

Toluene → [2-(Bicyclo[2.2.1]hept-5-en-2-yl)ethyl](trimethoxy)silane

https://huagongshe.com/reaction/402920

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantAmmonium BicarbonateHCID 14013—
ReactantTrimethoxysilaneHCID 17215—
Reactant5-Vinyl-2-norborneneHCID 18273—
Product[2-(Bicyclo[2.2.1]hept-5-en-2-yl)ethyl](trimethoxy)silaneHCID 22388779—
Product5-VinylnorbornyltrimethoxysilaneHCID 86678241—

Reaction Steps

A flask equipped with a thermometer, condenser, stirrer and dropping funnel was charged with 120 g (1.0 mole) of 5-vinyl-2-norbornene, an amount (1×10−4 mole of platinum atoms per mole of 5-vinyl-2-norbornene) of toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, and 0.4 g (0.005 mole) of ammonium hydrogencarbonate. To the flask at an internal temperature of 55-65° C., 124 g (1.0 mole) of trimethoxysilane was added dropwise over 4 hours. The contents were stirred for one hour at the temperature. On analysis by gas chromatography, the percentage conversion of 5-vinyl-2-norbornene was 98%. The ratio in area % of 5-(2-trimethoxysilylethyl)-2-norbornene:5-vinylnorbornyltrimethoxysilane:bissilyl adduct formed by addition to both endocyclic olefin and vinyl was 95.3:0.1:4.6. The reaction solution was distilled, collecting 218 g of 5-(2-trimethoxysilylethyl)-2-norbornene at a boiling point of 102-103° C./0.4 kPa (yield 90%, purity 99.9%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08742155B2
Source datasetuspto-grants-2014_06
ORD IDord-8dcfae75ae7c488f9fdce060afbd9910
Source noteuspto-grants-2014_06