反应详情

温度

0 °C

1-(1-Ethyl-6-methoxy-1-H-indole-3-yl)ethanone oxime (100 mg, 0.43 mmol) was dissolved in THF (900 μL) at 0° C. n-BuLi (450 μL, 2.5 M in hexanes, 1.12 mol) was added dropwise, resulting in instant precipitation of solids. DMF (70 μL, 0.9 mol) in 260 μL of was then added dropwise. This was stirred at 0° C. for 1 h, then at room temperature for 1 h. The reaction mixture was pipetted into a mixture containing 1 mL of H2O, 1 mL of THF, and 100 μL of concentrated H2 SO4. This mixture was heated at 75° C. for 1 h and then was partitioned between H2O and EtOAc. The organic phase was dried and concentrated. Purification by column chromatography (CH2Cl2) yielded 1-ethyl-3-isoxazol-3-yl-6-methoxy-1-H-indole product as a white solid (13 mg, 12%).

1. additionwas added dropwise
2. customresulting in instant precipitation of solids
3. waitat room temperature for 1 h
4. temperatureThis mixture was heated at 75° C. for 1 h
5. customwas partitioned between H2O and EtOAc
6. customThe organic phase was dried
7. concentrationconcentrated
8. customPurification by column chromatography (CH2Cl2)