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ChemicalBook CAS DataBase List 3-(2-(triMethylsilyl)ethynyl)phenol

3-(2-(triMethylsilyl)ethynyl)phenol synthesis

2synthesis methods
-

Yield:388061-72-1 100%

Reaction Conditions:

with bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;triethylamine in tetrahydrofuran at 20; for 24 h;Cooling with ice;

Steps:

3-(3-(trimethylsilyl)prop-1-yn-1-yl)phenol (12):

To a solution of 3-iodophenol (44g), CuI (1.5g), PdCl2 (PPh3)2 (4.2g) in triethylamine (60ml) and THF (300ml) under ice-water bath was added ethynyltrimethylsilane (24g) dropwise to keep the temperature below 5. Upon completion the resulting mixture was transferred to rt for 24h and then filtered. The filtrate was purified on a silica column to give 12 as dark brown liquid. (38g, 100%). This was used without further purification.

References:

Liu, Jia-Kuo;Gu, Wei;Cheng, Xiao-Rui;Cheng, Jun-Ping;Zhou, Wen-Xia;Nie, Ai-Hua [Chinese Chemical Letters,2015,vol. 26,# 10,p. 1327 - 1330] Location in patent:supporting information