(2-Bromoethyl)cyclohexane → 1-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde

HRID 51297

Reaction equation

HRID 51297 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH:10]1([CH2:16][CH2:17]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH:10]1([CH2:16][CH2:17][N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 222898451-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazole-4-carboxaldehyde (4.8 g, 50 mmol) was added portionwise to a suspension of sodium hydride (2.20 g, 60% dispersion in mineral oil, 55 mmol) in tetrahydrofuran (150 ml), and the mixture was then stirred at room temperature for 1 hour. 2-Cyclohexylethyl bromide (8.6 ml, 55 mmol) was added, and the mixture was heated under reflux for 18 hours. The cooled mixture was evaporated under reduced pressure and the residue was partitioned between water (500 ml) and dichloromethane (500 ml). The layers were separated, and the organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4) to afford the title compound, 1.78 g. 1H-NMR (CDCl3, 400 MHz) δ: 0.98 (m, 2H), 1.20 (m, 4H), 1.68 (m, 7H), 4.00 (t, 2H), 7.4 (s, 1H), 7.60 (s, 1H), 9.80 (s, 1H). LRMS: m/z (TSP+) 207.2 [MH+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe cooled mixture was evaporated under reduced pressure
  4. customthe residue was partitioned between water (500 ml) and dichloromethane (500 ml)
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4)

Sources & evidence

ORD record
ord-33dff91b72c14abda21f5070743bc992
Source dataset
uspto-grants-2004_03
Patent number
US06713496B2

Linked notes

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