反应详情

To a solution of 3,6-bis-allyloxy-5-nitrobenzo[d]isoxazole (0.60 g, 2.17 mmol) in EtOAc (12 mL) is added portionwise tin(II) chloride dihydrate (2.2 g, 9.75 mmol). The mixture is stirred at room temperature for 2 h and then at 60° C. for 1.5 h. The mixture is diluted with EtOAc and saturated NaHCO3 is added dropwise, resulting in the formation of a precipitate. Sodium carbonate (2N) is added and the insoluble precipitate is filtered off. The phases are separated and the aqueous phase is extracted with EtOAc (3×). The organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated. The crude material is purified by flash chromatography on silica gel, eluting with a gradient of hexanes/EtOAc to afford 3,6-bis-allyloxybenzo[d]isoxazol-5-ylamine as a waxy solid: (M+H)+=247.2.

1. waitat 60° C. for 1.5 h
2. additionis added dropwise
3. customresulting in the formation of a precipitate
4. filtrationthe insoluble precipitate is filtered off
5. customThe phases are separated
6. extractionthe aqueous phase is extracted with EtOAc (3×)
7. washThe organic layers are washed with water and brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude material is purified by flash chromatography on silica gel
12. washeluting with a gradient of hexanes/EtOAc