반응 #1563861

반응 방정식

2-bromofuran

diisopropylamine

THF

trimethylsilyl acetylene

→

(furan-2-ylethynyl)trimethylsilane

수율 35.8%

용매

water

반응 조건

후처리

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

실험 절차

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%).

출처