Sodium Hydroxide → 2-(2,6-diethyl-benzyl)-1H-imidazole

HRID 254529Notes

Reaction equation

HRID 254529 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[CH:11]([C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)O)[CH3:2].[OH-].[Na+]>Cl.[Zn]>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[CH2:11][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58951693(2,6-diethyl-phenyl)-(1H-imidazol-2-yl)-methanol

Product 1

HCID 247818692-(2,6-diethyl-benzyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 90 mg (0.39 mmol) (2,6-diethyl-phenyl)-(1H-imidazol-2-yl)-methanol (Example 96) in 2 ml concentrated aqueous HCl solution were added 500 mg zinc foil and heated to reflux for 20 hours. Then the mixture was cooled to ambient temperature, aqueous sodium hydroxide solution added, the turbid solution filtered and the filtrate extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. 2-(2,6-Diethyl-benzyl)-1H-imidazole was obtained as off-white solid: MS (EI): 214.3 (M+.).

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. filtrationthe turbid solution filtered
  4. extractionthe filtrate extracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-33c18b7f7683461da07fc1f2e92cb67d
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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