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

HRID 1723279Notes

Reaction equation

HRID 1723279 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 and the solid was washed with hot chloroform (1 l). The combined filtrates were evaporated in vacuo to leave a solid (4.0 g) which was purified by FCC eluting with chloroform to give a solid which was triturated with hexane (ca. 50 ml) to give the title compound (2.99 g), m.p. 184°-188° (decomp.).

Workup

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

Sources & evidence

ORD record
ord-2eb04d87a4f24e92b6e7739db1d98c28
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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