1,1'-Carbonyldiimidazole → Ethyl β-oxo-1H-imidazole-1-hexanoate
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- additionwas added
- stirringthe mixture was stirred at room temperature for 18 more hours
- concentrationAfter the reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in dichloromethane
- washThe dichloromethane layer was washed with water
- dry with materialdried (MgSO4)
- distillationafter which the solvent was distilled off
- washeluted with chloroform-methanol (30:1
Sources & evidence
- ORD record
- ord-3bbe189927fc4c66aa0e05d54c9d5a27
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05770602
Reaction notes
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