Water → HCID 57731304, compound

HRID 1010521Notes

Reaction equation

HRID 1010521 reaction equation
[CH2:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)[CH3:2].CC([O-])(C)C.[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].O>C1COCC1.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:6]1[CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=[CH:5]1)[CH3:20].[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:4]1[C:3]([CH2:1][CH3:2])=[CH:7][N:6]=[CH:5]1)[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 178437183HCID 178437183, compound

Product 2

HCID 57731304HCID 57731304, compoundHCID 57731307HCID 57731307, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.02 g (50 mmol) of 4-ethylimidazole are dissolved in 100 ml THF at rt under nitrogen. 5.9 g (52 mmol) KOtBu is added and the reaction is stirred for 2 h at rt. 6.3 ml (55 mmol) ethyl bromoacetate is added drop wise over a period of 30 min and the resulting mixture is stirred at rt for 2.5 h. 20 ml H2O and 130 ml AcOEt are added, the organic layer is separated and the aq. layer is washed again 2× with 100 ml AcOEt. The combined organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo. The reaction is purified by Flash-chromatography (silica gel, MeOH/methylen chloride) to give (4-ethyl-imidazol-1-yl)-acetic acid ethyl ester and (5-ethyl-imidazol-1-yl)-acetic acid ethyl ester, respectively.

Workup

  1. stirringthe resulting mixture is stirred at rt for 2.5 h
  2. customthe organic layer is separated
  3. washthe aq. layer is washed again 2× with 100 ml AcOEt
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe reaction is purified by Flash-chromatography (silica gel, MeOH/methylen chloride)

Sources & evidence

ORD record
ord-ea5d86e6793f4f59865c35c4fa6c3f67
Source dataset
uspto-grants-2011_07
Patent number
US07977323B2

Reaction notes

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