Реакция #1563863

Уравнение реакции

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   Экстракцияextracted with dichloromethane
3. 3
   ПромывкаThe combined organic layers were washed with brine
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   Другоеthe solvent was evaporated
6. 6
   ДругоеThe crude material was purified by column chromatography (100-200 mesh silica gel)

Методика

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%).

Источник