反応 #1563863

反応方程式

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

溶媒

THF

反応条件

後処理

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

実験手順

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%).

出典