反应详情

To a stirred solution of compound 83 (270 mg, 0.37 mmol) in chloroform (7 mL), was added during 4 h, a solution of diiodine (192 mg, 0.76 mmol) in chloroform (14 mL), dropwise. The mixture was then stirred 14 h at room temperature before addition of an aqueous saturated sodium carbonate solution (40 mL). The solution was decanted and the organic layer was washed with a 5% aqueous sodium hydrogenosulfite solution (2×15 mL), dried on magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed (Al2O3, AcOEt/cyclohexane, 7/3, v/v) to give compound 84 (112 mg, 0.20 mmol) as a yellow oil. Yield 54%; Rf (Al2O3, AcOEt/cyclohexane, 7/3, v/v) 0.68; IR (CCl4) ν 1119, 1189, 1246, 1286, 1458, 1509, 1649, 2800-3000, 3246 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.14 (t, 3H, J=7.1 Hz), 2.86 (m, 4H), 3.05 (t, 2H, J=5.5 Hz), 3.76 (q, 2H, J=5.5 Hz), 4.10 (t, 2H, J=5.5 Hz), 6.80 (dd, 1H, J=4.9, 7.9 Hz), 6.97 (m, 1H), 7.53 (m, 1H), 7.83 (dd, 1H, J=1.4, 9.2 Hz), 7.93 (m, 2H), 8.25 (dd, 1H, J=1.5, 8.7 Hz), 8.60 (se, 1H), 8.92 (dd, 1H, J=1.5, 7.2 Hz), 10.92 (m, 1H); ESI-MS m/z 560.0 [M+H]+.

1. customThe solution was decanted
2. washthe organic layer was washed with a 5% aqueous sodium hydrogenosulfite solution (2×15 mL)
3. customdried on magnesium sulfate
4. filtrationfiltered
5. customevaporated under vacuum
6. customThe residue was chromatographed (Al2O3, AcOEt/cyclohexane, 7/3