反应详情

A solution of the product from Example 132B (1 g, 4.92 mmol) in acetone (150 ml) was added 15% MgSO4 (15 mL). To the solution was added KMnO4 (1.944 g, 12.30 mmol) and stirred at ambient temperature for 2 hours. Then heated at slightly reflux for 40 hours. The mixture was filtered through diatomaceous earth, and washed with CH2Cl2. The organic was separated, diluted with CH2Cl2, washed with saturated Na2S2O3, dried and concentrated. The residue was purified by chromatography on silica gel column eluting with 20% EtOAc/hexanes to provide the title product. 1H NMR (DMSO-d6) δ 1.68-1.74 (m, 4H), 1.94 (s, 3H), 2.55-2.59 (m, 2H), 2.70 (t, J=6.04 Hz, 2H), 6.98 (d, J=7.34 Hz, 1H), 7.22 (d, J=7.34 Hz, 1H), 7.32 (t, J=7.70 Hz, 1H), 9.90 (s, 1H). MS (M+H)+ m/z 218.

1. temperatureThen heated
2. temperatureat slightly reflux for 40 hours
3. filtrationThe mixture was filtered through diatomaceous earth
4. washwashed with CH2Cl2
5. customThe organic was separated
6. additiondiluted with CH2Cl2
7. washwashed with saturated Na2S2O3
8. customdried
9. concentrationconcentrated
10. customThe residue was purified by chromatography on silica gel column
11. washeluting with 20% EtOAc/hexanes