تفاعل #792186

معادلة التفاعل

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر