反应详情

To a solution of 2,2-dimethyl-7-nitrobenzopyran (11.1 g, 53.9 mmol) in ethyl acetate (165 mL), (Cyc, Ph)-salen manganese complex (XX) (405 mg, 0.431 mmol) and N-methyl imidazole (858 μL, 10.8 mmol) were added, and sodium hypochlorite aqueous solution (101 g, 162 mmol) was added dropwise at 20° C. thereto over 15 minutes. After stirring the resulting mixture at room temperature for 3 hours, saturated sodium thiosulfate aqueous solution was added thereto under cooling with water. The resulting reaction solution was filtered through celite, the organic phase was washed with saturated sodium thiosulfate aqueous solution and saturated sodium chloride solution, and then dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting solid was recrystallized in ethanol to obtain (3R*,4R*)-3,4-epoxy-2,2-dimethyl-7-nitro-3-chromanol (yield: 66%).

1. customThe resulting reaction solution
2. filtrationwas filtered through celite
3. washthe organic phase was washed with saturated sodium thiosulfate aqueous solution and saturated sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under a reduced pressure
6. customThe resulting solid was recrystallized in ethanol