Iodine → 3,5-diethyl 4-iodo-1H-pyrazole-3,5-dicarboxylate

反応式

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[I:16]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:14]([O:13][C:11]([C:9]1[C:10]([I:16])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:7][N:8]=1)=[O:12])[CH3:15]

参加物

実験手順

To a solution of 10 g 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester in 400 ml acetonitrile 13 g ammonium cerium(iv) nitrate (CAN) and 7.17 g iodine were added and the mixture was heated to reflux for 5 h. Then, after cooling to RT, 30 ml sat. sodium thiosulfate solution were added. The mixture was extracted with ethyl acetate (3×100 ml), the combined organic layers were washed with water and then dried over MgSO4, filtered and the solvents were removed under reduced pressure. The residue was filtered through a pad of silica gel eluting with heptane/ethyl acetate 1:1.