Toluene → [2-(Bicyclo[2.2.1]hept-5-en-2-yl)ethyl](trimethoxy)silane
Reaction equation
[CH:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)=[CH2:2].C1(C)C=CC=CC=1.C(=O)([O-])O.[NH4+].[CH3:22][O:23][SiH:24]([O:27][CH3:28])[O:25][CH3:26]>>[CH3:22][O:23][Si:24]([O:27][CH3:28])([O:25][CH3:26])[CH2:2][CH2:1][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2.[CH:1]([CH:3]1[CH2:8][C:7]2([Si:24]([O:27][CH3:28])([O:25][CH3:26])[O:23][CH3:22])[CH2:9][CH:4]1[CH2:5][CH2:6]2)=[CH2:2]Participants
Procedure
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%).
Workup
- customA flask equipped with a thermometer, condenser, stirrer
Sources & evidence
- ORD record
- ord-8dcfae75ae7c488f9fdce060afbd9910
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742155B2
Reaction notes
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