1-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde → 1-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethyl-2-methyl-1H-imidazole-5-carbaldehyde

HRID 1828819Notes

Reaction equation

HRID 1828819 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]([CH:10]=[O:11])=[C:8]([CH:12]=[CH2:13])[N:7]=[C:6]1[CH3:14]>O1CCOCC1.[C].[Pd]>[Cl:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]([CH:10]=[O:11])=[C:8]([CH2:12][CH3:13])[N:7]=[C:6]1[CH3:14]

Participants

4

Reactant 1

HCID 220586901-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 220586571-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethyl-2-methyl-1H-imidazole-5-carbaldehydeYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-(2-Chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde (575 mg) was dissolved in 1,4-dioxane (6 ml) and palladium carbon (50 mg) was added. The mixture was stirred under a hydrogen atmosphere for 1.5 hr. The reaction mixture was filtered through celite. Water was added to the filtrate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with chloroform/ethyl acetate=2/1. The objective fraction was concentrated under reduced pressure to give 1-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethyl-2-methyl-1H-imidazole-5-carbaldehyde (283 mg) as a black brown oil.

Workup

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

Sources & evidence

ORD record
ord-780b3400cac64ca7bf9d1775b0856bda
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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