反应详情

A mixture of 0.1 mol of 4-pentyliodobenzene, 0.12 mol of trimetylsilylacetylene, 0.0014 mol of bis(triphenylphosphine)-palladium(II) Chloride Pd(PPh3)2Cl2 and 0.7 mmol of copper (I) iodide in 250 ml diethylamine is stirred at room temperature for 20 hours. After evaporation of the solvent the crude product is purified by chromatography on alumina (4:1 petrol/dichloromethane) to give 2-(4-pentylphenyl)-1-trimethylsilyacetylene. Removal of the trimethylsilylgroup is accomplished by treatment this acetylene is methanol with 1 M KOH for 1 hour at room temperature. Evaporation of the methanol and either extraction yields 4-pentylphenylacetylene.

1. customAfter evaporation of the solvent the crude product
2. customis purified by chromatography on alumina (4:1 petrol/dichloromethane)
3. customto give 2-(4-pentylphenyl)-1-trimethylsilyacetylene
4. customRemoval of the trimethylsilylgroup
5. customfor 1 hour
6. customat room temperature
7. customEvaporation of the methanol
8. extractioneither extraction