Reaction #792184

Reaction equation

2-bromofuran

diisopropylamine

THF

trimethylsilyl acetylene

→

(furan-2-ylethynyl)trimethylsilane

Yield 35.8%

Solvents

water

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-bromofuran (500 mg, 3.402 mmol), Pd(PPh3)2Cl2 (75.69 mg, 0.10784 mmol), CuI (40.17 mg, 0.2109 mmol) and diisopropylamine (0.89 ml, 6.395 mmol) in tetrahydrofuaran (THF) (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.648 ml, 4.694 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 the desired (furan-2-ylethynyl)trimethylsilane (200 mg, 1.21 mmol, yield 35.84%).

Source