反应详情

温度

80 °C

A 100-mL round-bottom flask equipped with a magnetic stir bar, a rubber septum and N2 inlet was charged with 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazole (3.5 g, 12.4 mmol), Pd(Ph3P)2Cl2 (0.87 g, 1.24 mmol), CuI (0.47 g, 0.48 mmol), and triethylamine (62 mL). This mixture was degassed with three vacuum/N2 cycles. Trimethylsilylacetylene (3.5 mL, 24.8 mmol) was added, and the mixture was heated at 80° C. for 4 h. The reaction was monitored by LCMS. Upon completion, the reaction mixture was cooled down to room temperature, filtered through Celite, washed with ethyl acetate (100 mL), and concentrated. The crude product was purified on a silica gel column eluting with 5% ethyl acetate in hexanes to afford the title compound as a pale yellow oil (3.6 g). LCMS: 216 [(M-THP+H)+H]+.

1. customA 100-mL round-bottom flask equipped with a magnetic stir bar
2. customThis mixture was degassed with three vacuum/N2 cycles
3. temperatureUpon completion, the reaction mixture was cooled down to room temperature
4. filtrationfiltered through Celite
5. washwashed with ethyl acetate (100 mL)
6. concentrationconcentrated
7. customThe crude product was purified on a silica gel column
8. washeluting with 5% ethyl acetate in hexanes