反应详情

In a shaded container, 2a-(4-pentenyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (1.3 g, 5.3 mmol) and N-methylmorpholine oxide (1.9 g, 16 mmol) were dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml), and the solution was mixed with osmium tetroxide (4% aqueous solution 3.4 ml, 0.53 mmol) and stirred at room temperature for 2 hours. The reaction solution was mixed with rater (80 ml), the reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure. The residue was dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml), and the solution was mixed with sodium periodate (2.6 g, 12 mmol) and stirred as such for 2.5 hours. The reaction solution was mixed with water (100 ml), and the reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. By evaporating the solvent from the extract under a reduced pressure, 1.3 g (5.3 mmol 100% in yield) of the title compound was obtained.

1. additionThe reaction solution was mixed with rater (80 ml)
2. extractionthe reaction product was extracted with ethyl acetate
3. washwashed with saturated brine
4. dry with materialdried with anhydrous sodium sulfate
5. customthe solvent was removed by evaporation under a reduced pressure
6. dissolutionThe residue was dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml)
7. stirringstirred as such for 2.5 hours
8. extractionthe reaction product was extracted with ethyl acetate
9. washwashed with saturated brine
10. dry with materialdried with anhydrous sodium sulfate
11. customBy evaporating the solvent from the
12. extractionextract under a reduced pressure, 1.3 g (5.3 mmol 100% in yield) of the title compound
13. customwas obtained