Réaction #792186

Équation de réaction

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source