1-(1-trityl-1H-imidazol-4-yl)ethanol → 1-(1-trityl-1H-imidazol-4-yl)ethanone

HRID 1194368Notes

Reaction equation

HRID 1194368 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([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:8]=1)[OH:3]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:22]1([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)[N:7]2[CH:8]=[C:4]([C:2](=[O:3])[CH3:1])[N:5]=[CH:6]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 123447941-(1-trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanoneYield 58%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 221.3 g (2.544 moles) of manganese dioxide and 56.9 g (0.161 mole) of alpha-methyl-1-triphenylmethyl-1H-imidazole-4-methanol dissolved in 2.5 liters of chloroform is heated under reflux for 90 minutes. The solution is then cooled to about 50° C., filtered and the chloroform is eliminated by distillation. The residue is dissolved in 400 ml of isopropyl alcohol and filtered hot on Norit. The product crystallizes upon cooling. There are obtained 32.8 g of 1-(1-triphenylmethyl-1H-imidazol-4-yl)-1-ethanone. Yield: 58% of theory; M.P.: 158°-160° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 90 minutes
  3. filtrationfiltered
  4. distillationthe chloroform is eliminated by distillation
  5. dissolutionThe residue is dissolved in 400 ml of isopropyl alcohol
  6. filtrationfiltered hot on Norit
  7. customThe product crystallizes
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-5dcd543da69e4d80b9b41f11833273dc
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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