反应详情

A round bottom flask was flame-dried under high vacuum. The vacuum was broken by the addition of dry argon, and the flask was allowed to cool to room temperature. The flask was charged with 2.16 g (5.0 mmol) of (5-bromothiophen-2-yl)methyl tert-butyldiphenylsilyl ether (Compound 12), 2.12 mL (15 mmol) of (trimethylsilyl)acetylene, and 17.5 mL of triethylamine. The solution was purged with argon for 15 min and bis(triphenylphosphine)palladium (II) chloride (88 mg, 0.125 mmol) and copper (I) iodide (24 mg, 0.125 mmol) were added and the solution stirred at ambient temperature for 3 days. The solution was poured into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted 3 times with ether. The combined ether layers were washed once with brine, and dried over magnesium sulfate, and the solvents were removed under reduced pressure. The residue was purified by silica gel chromatography (hexane) to give the title compound.

1. customA round bottom flask was flame-dried under high vacuum
2. additionThe vacuum was broken by the addition of dry argon
3. customThe solution was purged with argon for 15 min
4. additionThe solution was poured into a separatory funnel
5. customThe layers were separated
6. extractionthe aqueous layer was extracted 3 times with ether
7. washThe combined ether layers were washed once with brine
8. dry with materialdried over magnesium sulfate
9. customthe solvents were removed under reduced pressure
10. customThe residue was purified by silica gel chromatography (hexane)