5-(hydroxy methyl)-2-propyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole → 4-(2,5-dimethyl-1H-pyrrol 1-yl)-2-propylimidazole-5-carboxaldehyde

HRID 248640Notes

Reaction equation

HRID 248640 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]([CH2:8][CH2:9][CH3:10])=[N:5][C:4]=1[N:11]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]1[CH3:17]>C1COCC1.O=[Mn]=O>[CH3:17][C:12]1[N:11]([C:4]2[N:5]=[C:6]([CH2:8][CH2:9][CH3:10])[NH:7][C:3]=2[CH:2]=[O:1])[C:15]([CH3:16])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 149628935-(hydroxy methyl)-2-propyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole

Product 1

HCID 149628924-(2,5-dimethyl-1H-pyrrol 1-yl)-2-propylimidazole-5-carboxaldehydeYield 75%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(hydroxy-methyl)-2-propyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole (Example 48, 6.0 g, 0.026 mol) in dry THF (125 mL) was added MnO2 (11.2 g, 0.13 mol) and the reaction mixture refluxed for 4 hours under an atmosphere of nitrogen. The reaction mixture was cooled, filtered through celite, and the resulting filtrate evaporated under reduced pressure. Purification by flash chromatography (silica; 2:1 hexane ethyl acetate) gave the title compound 4-(2,5-dimethyl-1H-pyrrol 1-yl)-2-propylimidazole-5-carboxaldehyde (4.5 g, 75%), mp 119°-121° C.

Workup

  1. temperaturethe reaction mixture refluxed for 4 hours under an atmosphere of nitrogen
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. customthe resulting filtrate evaporated under reduced pressure
  5. customPurification by flash chromatography (silica; 2:1 hexane ethyl acetate)

Sources & evidence

ORD record
ord-f7400e04e5fa4143bf49ca81293e0c03
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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