反应 #1563863

反应方程式

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   萃取extracted with dichloromethane
3. 3
   洗涤The combined organic layers were washed with brine
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   其他the solvent was evaporated
6. 6
   其他The crude material was purified by column chromatography (100-200 mesh silica gel)

实验过程

A mixture of 2-iodothiophene (500 mg, 2.38 mmol), Pd(PPh3)2Cl2 (52.95 mg, 0.0754 mmol), CuI (28.1 mg, 0.14756 mmol) and diisopropylamine (0.62 ml, 4.4744 mmol) in THF (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.453 ml, 3.284 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield 300 mg of trimethyl(thiophen-2-ylethynyl)silane (300 mg, 1.66 mol, yield 70.02%).

来源