反应详情

温度

0 °C

To a suspension of sodium hydride (326 mg, 8.10 mmol) in DMF (13 mL) at 0° C. was added a solution of (1H-Indol-3-yl)-acetic acid methyl ester (1.0 g, 5.3 mmol) in DMSO (3 mL). The mixture was stirred at 0° C. for 30 min and then at rt for 1 h. The reaction mixture was cooled back down to 0° C., and SEMCl (1.35 mL, 8.41 mmol) was added neat. The reaction mixture was stirred at 0° C. for 15 min and then at rt for 1 h. The reaction mixture was then partitioned between water (200 mL) and diethyl ether (200 mL) followed by further extraction of the water layer with ether (2×200 mL) and drying of the combined organic layers with Na2SO4. After removal of the solvent under reduced pressure, the crude material was purified by flash chromatography (EtOAc/hexanes) giving 1.1 g (70%) of [1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-3yl]-acetic acid methyl ester. 1H NMR (400 MHz, CDCl3): 7.65 (d, J=7.8 Hz, 1H), 7.46 (d, J=8.1, 1H), 7.26 (m, 1H), 7.22 (m, 2H), 5.51 (s, 2H), 3.83 (s, 2H), 3.76 (s, 3H), 3.53 (t, J=7.9 Hz, 2H), 0.94 (t, J=7.9 Hz, 2H), 0.0 (s, 9H).

1. waitat rt for 1 h
2. additionwas added neat
3. stirringThe reaction mixture was stirred at 0° C. for 15 min
4. waitat rt for 1 h
5. customThe reaction mixture was then partitioned between water (200 mL) and diethyl ether (200 mL)
6. extractionfollowed by further extraction of the water layer with ether (2×200 mL)
7. dry with materialdrying of the combined organic layers with Na2SO4
8. customAfter removal of the solvent under reduced pressure
9. customthe crude material was purified by flash chromatography (EtOAc/hexanes)