反应详情

A 16 ml portion of methanol solution of 6-acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (0.60 g, 1.64 mmol) was mixed with sodium methoxide and stirred at a room temperature for 3 hours. After neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration and the solvent was evaporated under a reduced pressure. The thus obtained oily substance was dissolved in 4 ml of acetone, and the solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with 1 N hydrochloric acid. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (100 cc; elution with ethyl acetate-hexane=1:2) to obtain 0.31 g of the title compound (56% in yield).

1. customAfter neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration
2. customthe solvent was evaporated under a reduced pressure
3. dissolutionThe thus obtained oily substance was dissolved in 4 ml of acetone
4. additionthe solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution
5. stirringstirred overnight at room temperature
6. extractionThe reaction solution was extracted with ethyl acetate
7. washwashed with 1 N hydrochloric acid
8. dry with materialAfter drying (Na2SO4)
9. customthe solvent was evaporated under a reduced pressure
10. customthe thus obtained oily substance was purified by a silica gel column chromatography (100 cc; elution with ethyl acetate-hexane=1:2)