1,1'-Carbonyldiimidazole → Ethyl β-oxo-1H-imidazole-1-hexanoate

HRID 1648262Notes

Reaction equation

HRID 1648262 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:24]([O:26][C:27](=[O:32])[CH2:28]C(O)=O)[CH3:25]>O1CCCC1>[CH2:24]([O:26][C:27](=[O:32])[CH2:28][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH3:25]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70615Monoethyl malonateHCID 3055390Imidazole-1-butyric acid

Product 1

HCID 22097627Ethyl β-oxo-1H-imidazole-1-hexanoateYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(1-imidazolyl)butyric acid (0.5 g) in tetrahydrofuran (35 ml), 1,1'-carbonyldiimidazole (0.578 g) was added, followed by stirring at room temperature for 6 hours. After magnesium salt of malonic acid monoethyl ester [Mg(OCOCH2COOC2H5)2 ] (1.02 g) was added, the mixture was stirred at room temperature for 18 more hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in dichloromethane. The dichloromethane layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residual oily substance was subjected to silica gel column chromatography and eluted with chloroform-methanol (30:1, v/v) to yield 6-(1-imidazolyl)-3-oxohexanoic acid ethyl ester (0.32 g, 44%) as an oily substance.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 18 more hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off
  8. washeluted with chloroform-methanol (30:1

Sources & evidence

ORD record
ord-4ac9d04d28c9430697401faf3f73566f
Source dataset
uspto-grants-1995_07
Patent number
US05436247

Reaction notes

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