反应详情

温度

57.5 °C

The compound 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (0.1 g, 0.18 mmol) synthesized in Step 1 of Examples 14 and 15, CS2CO3 (0.36 g, 0.54 mmol), and anhydrous acetone (20 mL) were charged to a dry round-bottom flask. Under stirring, epichlorohydrin (0.2 g, 1.08 mmol) was added thereto using a syringe. The reaction liquid was stirred with reflux at a temperature of 55 to 60° C. under a nitrogen atmosphere (48 h). Solid of the reaction mixture was filtered and removed. The filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give a yellow solid compound 11-hydroxy-9-(oxiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (24.3 mg, 20.3%) and a yellow solid compound 9,11-bis(oxiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (32 mg, 22.1%).

1. customThe reaction liquid
2. stirringwas stirred
3. filtrationSolid of the reaction mixture was filtered
4. customremoved
5. concentrationThe filtrate was concentrated under reduced pressure
6. customThe resulting residue was separated
7. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))