반응 #1563863

반응 방정식

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

용매

THF

반응 조건

후처리

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

실험 절차

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%).

출처