反应详情

温度

0 °C

A 50 mL round-bottomed flask equipped with a magnetic stirrer was charged with 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole (0.600 g, 0.002 mol), 25 mL of anhydrous acetonitrile and potassium carbonate (1.104 g, 0.008 mol). The reaction mixture was cooled to 0° C. and iodoacetonitrile (0.500 g, 0.003 mol) was added dropwise over five minutes. The reaction mixture was allowed to warm to ambient temperature and stirred for eighteen hours. The mixture was taken in ether (200 mL), washed with water (2×30 mL) and brine (1×30 mL), dried over MgSO4 and concentrated in vacuo. The resulting oily brown residue was purified by flash chromatography (8:2 ethyl acetate/hexanes) to give [1-(2-fluoro-benzenesulfonyl)-1H-indol-4-yloxy]acetonitrile as a crystalline solid (0.507 g, 77%). 1H NMR (300 MHz, CDCl3) δ: 4.87 (s, 2 H), 6.76 (d, 1 H, J=13.18), 6.77 (d, 1 H, J=1.51), 7.11 (dt, 1 H, J=8.29, J=1.13), 7.23 (t, 1 H, J=8.29), 7.29 (dt, 1 H, J=7.73, J=1.13), 758 (m, 4 H), 8.03 (m, 1 H).

1. customA 50 mL round-bottomed flask equipped with a magnetic stirrer
2. temperatureto warm to ambient temperature
3. washwashed with water (2×30 mL) and brine (1×30 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe resulting oily brown residue was purified by flash chromatography (8:2 ethyl acetate/hexanes)