Sulfuric Acid → 10-Benzo[1,3]dioxol-5-yl-5-iodo-9H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-one

反応式

[I:1]N1C(=O)CCC1=O.OS(O)(=O)=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:39])[C:25]=4[CH:26]=[C:27]4[C:35]=3[C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=[CH:28]4)=[CH:22][C:17]=2[O:16][CH2:15]1>C(#N)C>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:39])[C:25]=4[CH:26]=[C:27]4[C:35]=3[C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=[C:28]4[I:1])=[CH:22][C:17]=2[O:16][CH2:15]1

参加物

実験手順

N-iodosuccinimide (13.6 mg, 0.06 mmol) and concentrated H2SO4 (5 μL) was added to a solution of 2 (14 mg, 0.04 mmol) in acetonitrile (1 mL). The mixture was stirred at room temperature for 36 h, concentrated at reduced pressure, and then diluted with ether (30 mL). The same workup and purification procedure as described for the isolation of 37 afforded 39 (10.5 mg, 55%) as a yellow powder. mp 255° C. (decomp.); 1H NMR (CDCl3) δ 8.78 (s, 1H, H4), 7.93 (s, 1H, H6), 6.75-6.90 (m, 3H, H2′+H5′+H6′), 6.08 (AB, 2H, 3′,4′-OCH2O—, Δδ=8.7 Hz, J=1.5 Hz), 5.97 (AB, 2H, 7,8-OCH2O—, Δδ=7.8 Hz, J=1.5 Hz), 5.23 (q, 2H, lactone-CH2—, J=8.7 Hz); MS (EI) m/z 474 [M]+.