Potassium Permanganate → 1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-1H-imidazole

HRID 1750913Notes

Reaction equation

HRID 1750913 reaction equation
[CH:1]([C:4]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]=1[N:20]1[CH2:24][CH2:23][N:22]=[C:21]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:3])[CH3:2].[O-][Mn](=O)(=O)=O.[K+].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C(#N)C>[CH:1]([C:4]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]=1[N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516875Potassium PermanganateHCID 584010671-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazoleHCID 71586775Bentonite

Product 1

HCID 584009361-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-1H-imidazoleYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazole (4.7 g, 12 mmol) was dissolved in 100 mL acetonitrile. To the stirred solution fine mixture of KMnO4 (3.8 g, 24 mmol) and 4 g montmorillonite K10 clay was added in small portions and the reaction mixture was stirred for 2 h. At the end, reaction was quenched with MeOH and filtered thru a Celite pad. Crude product was purified by flash chromatography over silica gel with 80% DCM/Hexane to 80% DCM/ethylacetate. 3 g light yellow color oil was isolated. This oil was further purified by reverse phase chromatography. Target compound (1.3 g, 28% yield) was isolated as white solid.

Workup

  1. additionwas added in small portions
  2. customAt the end, reaction
  3. customwas quenched with MeOH
  4. filtrationfiltered
  5. customCrude product was purified by flash chromatography over silica gel with 80% DCM/Hexane to 80% DCM/ethylacetate
  6. custom3 g light yellow color oil was isolated
  7. customThis oil was further purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ff526a3af51147ce8256648c4350b15c
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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