Acetic Acid → (E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-5-oxovaleric acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])/[C:5](=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]2)=[C:16]([O:26][CH3:27])[CH:15]=1)/[CH2:6][CH2:7][CH:8]1OCC[O:9]1)[CH3:2].C(O)(=O)C.FC(F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:28])/[C:5](=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]2)=[C:16]([O:26][CH3:27])[CH:15]=1)/[CH2:6][CH2:7][CH:8]=[O:9])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To an aqueous solution of (243 mg) of (E)-4-[1,3]dioxolan-2-yl-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]butyric acid ethyl ester, acetic acid (2 mL) and trifluoroacetic acid (2.0 mL) were added one by one, and the reaction solution was agitated at room temperature for 4 hours. After confirming disappearance of the starting materials, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and 110 mg of the title compound was obtained by condensing under reduced pressure. The physical properties of the compound are as follows.
Workup
- customthe organic layer was partitioned
- washAfter the obtained organic layer was washed with a saturated saline solution, it
- dry with materialwas dried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-8afad52672884b05982a5a899c0853f1
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687640B2
Reaction notes
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