Sodium hydride → 1-Propyl-1H-imidazole-4-carbaldehyde

HRID 70356Notes

Reaction equation

HRID 70356 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.I[CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:11]([N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 103517661-Propyl-1H-imidazole-4-carbaldehydeYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (95%, 231 mg, 9.18 mmol) in THF (20 ml) was added 4-imidazole carboxaldehyde (588 mg, 6.12 mmol) under ice cooling. The mixture was refluxed for 2 hours under nitrogen atmosphere. The mixture was cooled to room temperature and 1-iodopropane (5 ml) was added to the mixture and then refluxed for another 2 hours. The mixture was cooled down to rt and quenched with water. The solution was extracted with EtOAc (2×50 ml), washed with brine, dried over Na2SO4, concentrated in vacuo. The crude product was purified by column chromatography on silica gel (0-10% MeOH in CH2Cl2) to give the title compound (487 mg, 58%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours under nitrogen atmosphere
  2. temperaturerefluxed for another 2 hours
  3. temperatureThe mixture was cooled down to rt
  4. customquenched with water
  5. extractionThe solution was extracted with EtOAc (2×50 ml)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography on silica gel (0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-fff80cbcdcb5412196538a1a1cc06c5b
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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