反应详情

A solution of fuming nitric acid (15.0 mL, 358 mmol) in concentrated sulfuric acid (15.0 mL, 281 mmol) was added slowly over a period of 15 min. to a stirred solution of 4-iodo-2,3-dihydrofuro[2,3-b]pyridine (2.237 g, 9.055 mmol) in sulfuric acid (10.0 mL, 188 mmol) at −10° C. The reaction mixture was allowed to warm to room temperature, and stirred for a further 16 h. The reaction mixture was quenched by pouring onto crushed ice and was then extracted with EtOAc (6×100 mL). The organic extracts were combined and washed with saturated aq. NaHCO3 (2×300 mL) and brine (300 mL), then dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a pale yellow solid (2.43 g, 92%). LCMS calc. for C2H61N2O3 (M+H)+: m/z=292.9. found 293.0.

1. customThe reaction mixture was quenched
2. additionby pouring
3. customonto crushed ice
4. extractionwas then extracted with EtOAc (6×100 mL)
5. washwashed with saturated aq. NaHCO3 (2×300 mL) and brine (300 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)