2-TRIMETHYLSILYLANISOLE synthesis
- Product Name:2-TRIMETHYLSILYLANISOLE
- CAS Number:704-43-8
- Molecular formula:C10H16OSi
- Molecular Weight:180.32
Yield:704-43-8 99%
Reaction Conditions:
Stage #1: methoxybenzenewith n-butyllithium;N,N,N,N,-tetramethylethylenediamine in diethyl ether at 20; for 0.5 h;Schlenk technique;Inert atmosphere;
Stage #2: chloro-trimethyl-silane in diethyl ether;Schlenk technique;Inert atmosphere;Temperature;Reagent/catalyst;
Steps:
(2-Methoxyphenyl)trimethylsilane 7b
A 5 mL well-dried round-bottomed flask was charged with nitrogen through Schlenkline. To a solution of corresponding substrate (0.2 mmol) and TMEDA (34.8 mg, 1.5equiv.) in Et2O (0.4 M, 0.5 mL), nBuLi (2.4 M, 0.125 mL, 1.5 equiv.) was addeddropwise at room temperature. Then the reaction was allowed to stir for 0.5 h at room temperature. Then the reaction was quenched with 0.1 mL TMS-Cl, extracted withethyl acetate (5 mL x 3), dried over anhydrous Na2SO4, filtered and concentratedunder vacuo. The residue was purified by column chromatography to get the anisole7b as a colorless oil (34 mg, 95% yield).
References:
Xiong, Xiaoyu;Zhu, Ranran;Huang, Lin;Chang, Shuqin;Huang, Jianhui [Synlett,2017,vol. 28,# 15,art. no. ST-2017-W0237-L,p. 2046 - 2050] Location in patent:supporting information
1450-14-2
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766-51-8
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704-43-8
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