反应详情

6 g of 1-bromo-4-methylnaphthalene, 0.11 g of dichlorobis(triphenylphosphine)palladium, 0.17 g of triphenylphosphine, 0.19 g of copper iodide, and 3.1 g of trimethylsilylacetylene were added to 60 ml of triethylamine, and the mixture was allowed to react at 90° C. for 16 hours. After evaporation of the solvent by an evaporator, the compounds obtained were extracted with added ethyl ether. The ethyl ether layer was washed thrice with 300 ml of distilled water, dried over anhydrous magnesium sulfate for 24 hours, and filtered, and after removal of the solvent in the filtrate by vaporization, the residue was purified by column chromatography, by using hexane as the developing solvent. 30 ml of diethylene glycol and 4.4 g of potassium hydroxide were added to the compound obtained, and the mixture was stirred at room temperature for 3 hours. The compounds generated were extracted with added ethyl ether. The ethyl ether layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate for 24 hours and filtered, and the solvent in the filtrate was evaporated. The residue was purified by column chromatography by using methylene chloride/hexane (1/4) as the developing solvent, to give 1.6 g of 1-ethynyl-4-methylnaphthalene.

1. customto react at 90° C. for 16 hours
2. customAfter evaporation of the solvent
3. customby an evaporator
4. customthe compounds obtained
5. extractionwere extracted with added ethyl ether
6. washThe ethyl ether layer was washed thrice with 300 ml of distilled water
7. dry with materialdried over anhydrous magnesium sulfate for 24 hours
8. filtrationfiltered
9. customafter removal of the solvent in the filtrate by vaporization
10. customthe residue was purified by column chromatography
11. addition30 ml of diethylene glycol and 4.4 g of potassium hydroxide were added to the compound
12. customobtained
13. extractionThe compounds generated were extracted with added ethyl ether
14. washThe ethyl ether layer was washed twice with 300 ml of distilled water
15. dry with materialdried over anhydrous magnesium sulfate for 24 hours
16. filtrationfiltered
17. customthe solvent in the filtrate was evaporated
18. customThe residue was purified by column chromatography