(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol → 5-methyl-1-trityl-1H-imidazole-4-carbaldehyde

HRID 1382777Notes

Reaction equation

HRID 1382777 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][OH:27]>[O-2].[O-2].[Mn+4].O1CCOCC1>[CH3:1][C:2]1[N:6]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[N:4][C:3]=1[CH:26]=[O:27]

Participants

4

Reactant 1

HCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

Product 1

HCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehydeYield 100.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-methanol (4.0 g), manganese dioxide (activated) (40 g) and dioxan (225 ml) was stirred at room temperature overnight. The suspension was filtered through Hyflo, the solid washed with hot chloroform (1 l) and the combined filtrates evaporated in vacuo to leave an off-white solid (4.0 g). This solid was purified by FCC eluting with chloroform to give an off-white solid which was triturated with hexane (ca. 50 ml) to give the title compound (2.99 g) as a white crystalline solid, m.p. 184°-188° (decomp.).

Workup

  1. filtrationThe suspension was filtered through Hyflo
  2. washthe solid washed with hot chloroform (1 l)
  3. customthe combined filtrates evaporated in vacuo

Sources & evidence

ORD record
ord-7f5a3547c61045f0a12530e6072d03c3
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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