反应详情

温度

60 °C

A mixture of 3 (18.1 g, 45.9 mmol), Et3N (12.8 mL, 91.9 mmol), Pd(PPh)2Cl2 (1.6 g, 5% mol), CuI (0.7 g, 8% mol), and TMS-acetylene (19.6 mL, 137.8 mmol) in degassed THF (180 mL) is heated at 60° C. overnight. The mixture is cooled to rt, and then partitioned between H2O and EtOAc. This mixture is filtered through Celite to remove the insoluble material. The two layers of the filtrate are separated, and the organic layer is washed H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc as eluant to give 15.6 g (93%) of the product 4 as beige solid. 1H NMR (CDCl3) δ 7.15-7.00 (m, 2H), 6.41 (br s, 1H), 4.26 (q, J=7.1 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H), 0.27 (s, 9H); 19F NMR (CDCl3) δ −57.59 (s, 3F), −118.15 (s, 1F); MS 364 (M+1, 100%).

1. temperatureThe mixture is cooled to rt
2. custompartitioned between H2O and EtOAc
3. filtrationThis mixture is filtered through Celite
4. customto remove the insoluble material
5. customThe two layers of the filtrate are separated
6. washthe organic layer is washed H2O and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude material is purified on silica gel with heptane/EtOAc as eluant