2-Iodo-4-hydroxymethyl-1-(triphenylmethyl)imidazole → 2-Iodo-4-formyl-1-triphenylmethylimidazole
Reaction equation
[I:1][C:2]1[N:3]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[I:1][C:2]1[N:3]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1Participants
4
Procedure
The starting material can be prepared in the following manner. A mixture of 2-iodo-4-hydroxymethyl-1-(triphenylmethyl)imidazole (3.264 g, 7.0 mmol) and manganese dioxide (12.17 g, 140 mmol) in methylene chloride (100 mL) was stirred overnight at room temperature and filtered though Celite. The filtrate was concentrated in vacuo to give 2-iodo-4-formyl-1-triphenylmethylimidazole as a white foamy solid (3.05 g, 94%), mp 173-75° C. which was sufficiently pure to be used in the next step without further purification. 1H NMR (CDCl3) δ 9.77 (s, 1H), 7.55 (s, 1H), 7.38-7.30 (m, 9H), 7.16-7.09 (m, 6H).