Reaction #792186

Reaction equation

water

trimethylsilyl acetylene

2-iodothiophene

diisopropylamine

→

trimethyl(thiophen-2-ylethynyl)silane

Solvents

THF

Conditions

Workup

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

Procedure

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