Potassium Acetate → HCID 22058659, compound

HRID 1828820Notes

Reaction equation

HRID 1828820 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH:7]=[O:8].C([O-])(=O)C.[K+]>CO.O1CCOCC1.[C].[Pd]>[Cl:22][C:11]1[CH:12]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[CH:15][C:10]=1[CH2:9][N:5]1[C:6]([CH:7]=[O:8])=[CH:2][N:3]=[C:4]1[CH3:23]

Participants

6

Reactant 2

HCID 517044Potassium AcetateHCID 22058585HCID 22058585, compound

Product 1

HCID 22058659HCID 22058659, compoundYield 96.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (4.00 g) was dissolved in a mixed solvent of methanol (20 ml) and 1,4-dioxane (20 ml), and palladium carbon (400 mg) and potassium acetate (1.08 g) were added. The reaction mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with hexane/ethyl acetate=1/2. The objective fraction was concentrated under reduced pressure to give 1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (3.10 g) as a pale-yellow oil.

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with hexane/ethyl acetate=1/2
  10. concentrationThe objective fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b768588785534e989070cc119bbf6e5a
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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