反应详情

A solution of 3-triisopropylsilyoxy-1-bromonaphthalene (3.17 g, 8.4 mmol), 4-ethynyl-N,N-dibutylaniline (2.87 g, 12.5 mmol), Pd(PPh3)2Cl2 (176 mg, 3 mol %), PPh3 (329 mg, 15 mol %) and CuI (120 mg, 7.5 mol %) in Et3N (20 mL) under N2 was heated at reflux for 3 h. The resulting mixture was cooled, poured into water (200 mL), extracted with DCM (3×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using DCM (20% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue dissolved in Et2O (30 mL). Tetrabutylammonium fluoride (3.8 mL, 1 M, 3.8 mmol) was added and stirring continued for 10 min. The solution was poured into water (100 mL), extracted with Et2O (3×40 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (15% in hexanes to 0% in EtOAc gradient) as eluent. The solvent was removed under reduced pressure to give the title compound (1.40 g, 21%) as a brown oil.

1. temperatureat reflux for 3 h
2. temperatureThe resulting mixture was cooled
3. extractionextracted with DCM (3×50 mL)
4. dry with materialdried (MgSO4)
5. customthe solvent removed under reduced pressure
6. customThe residue was chromatographed on silica
7. customThe solvent was removed under reduced pressure
8. dissolutionthe residue dissolved in Et2O (30 mL)
9. extractionextracted with Et2O (3×40 mL)
10. dry with materialdried (MgSO4)
11. customthe solvent removed under reduced pressure
12. filtrationThe residue was filtered through a short plug of silica
13. customThe solvent was removed under reduced pressure