2-Iodo-4-hydroxymethyl-1-(triphenylmethyl)imidazole → 2-Iodo-4-formyl-1-triphenylmethylimidazole

HRID 1108275Notes

Reaction equation

HRID 1108275 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]=1

Participants

4

Reactant 1

HCID 187846252-Iodo-4-hydroxymethyl-1-(triphenylmethyl)imidazole

Product 1

HCID 187846372-Iodo-4-formyl-1-triphenylmethylimidazoleYield 94%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe starting material can be prepared in the following manner
  2. filtrationfiltered though Celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fae1343efa06497186eb4a4165c58342
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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