Pyridine, 2-(triethoxysilyl)- (9CI) synthesis
- Product Name:Pyridine, 2-(triethoxysilyl)- (9CI)
- CAS Number:213602-91-6
- Molecular formula:C11H19NO3Si
- Molecular Weight:241.36
Yield:213602-91-6 79%
Reaction Conditions:
with bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate;tetra-(n-butyl)ammonium iodide;triethylamine in N,N-dimethyl-formamide at 90; for 12 h;Inert atmosphere;
Steps:
Procedure for the synthesis of 2-triethyoxysilylpyridine (13)
2-Bromopyridine (11) (0.617ml, 6.33mmol), [Rh(cod)(MeCN)2]BF4 (72.2mg, 0.190mmol), TBAI (2.34g, 6.33mmol), triethylamine (2.65ml, 19.0mmol) and triethyoxysilane (12) (2.34ml, 12.7mmol) were combined. Degassed DMF (25ml) was added and the vessel was evacuated and backfilled with nitrogen three times. The mixture was stirred at 90 oC for 12 hours.The reaction mixture was diluted with diethyl ether (40ml) and extracted with water (3 x 20ml). The aqueous layer was further extracted with diethyl ether (30ml). The combined organic fractions were washed with brine (20ml), dried and the solvent evaporated under reduced pressure to obtain an orange oil. The crude was purified by flash chromatography (1:1 pentane: diethyl ether) to provide 1.21g (79% yield) of the product as a colourless oil.1H-NMR (400 MHz, CDCl3) δ 8.40-8.36 (m, 1H), 7.58-7.46 (m, 2H), 7.28-7.23 (m, 1H), 4.14-4.09 (m, 6H), 3.87-3.82 (m, 9H).
References:
Blakemore, David C.;Marples, Louise A. [Tetrahedron Letters,2011,vol. 52,# 32,p. 4192 - 4195] Location in patent:supporting information; experimental part
