反应详情

Trimethylsilylacetylene (4.1 mL, 28.8 mmol) and tetrakis(triphenylphosphine)palladium (0) (832 mg, 0.72 mmol) were added to a suspension of (1) (4.06 g, 14.4 mmol) and copper (I) iodide (274 mg, 1.44 mmol) in triethylamine (120 mL) that had been deoxygenated with argon. The mixture was deoxygenated with argon and then stirred under argon at room temperature for 40 hours. Aqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL), dried over anhydrous magnesium sulfate, filtered and then the solvent was completely removed. The residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent. The main band was isolated and the solvent completely removed to give (2) (2.59 g, 72%).

1. customhad been deoxygenated with argon
2. customThe mixture was deoxygenated with argon
3. additionAqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
6. washThe combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe solvent was completely removed
10. customThe residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent
11. customThe main band was isolated
12. customthe solvent completely removed