Imidazole → ethyl 2-(1H-imidazol-1-yl)propanoate

HRID 1386420Notes

Reaction equation

HRID 1386420 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C1COCC1>[N:3]1([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 18626501ethyl 2-(1H-imidazol-1-yl)propanoateYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 16.0 g (0.4 mol) of NaH.oil (60%) was washed with hexane to remove the oil and then resuspended in 400 mL of THF. This was then treated dropwise with a solution of 27:23 g (0.4 mol) of imidazole in 150 mL of THF and then refluxed for 1 hour. This was then treated dropwise with a solution of 72.4 g (0.4 mol) of ethyl 2-bromopropanoate in 100 mL of THF and the mixture heated at reflux for 2.5 hours. The mixture was filtered and the solvent removed under reduced pressure. The residue was taken up in Et2O and washed with H2O, then saturated NaCl. Drying over MgSO4 and treatment with charcoal gave the crude product. This was triturated with pentane and the pentane removed under reduced pressure to give 38.56 g (57.3% yield) of the product as an oil. The structure was confirmed by NMR and mass spectroscopy. MS m/z 169 (M+H+).

Workup

  1. washoil (60%) was washed with hexane
  2. customto remove the oil
  3. additionThis was then treated dropwise with a solution of 27
  4. temperaturethe mixture heated
  5. temperatureat reflux for 2.5 hours
  6. filtrationThe mixture was filtered
  7. customthe solvent removed under reduced pressure
  8. washwashed with H2O
  9. dry with materialDrying over MgSO4 and treatment with charcoal
  10. customgave the crude product
  11. customThis was triturated with pentane
  12. customthe pentane removed under reduced pressure

Sources & evidence

ORD record
ord-17763d6bc74042af9a1b8f1bfa807e1b
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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