Hydrochloric Acid → (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid
Reaction equation
C(OP([CH2:9][C:10]([O:12]CC)=[O:11])(OCC)=O)C.O.[OH-].[Li+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1)[CH:23]=O.[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[CH:23]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Ethyl diethylphosphonoacetate (5.7 g) and lithium hydroxide monohydrate (1.3 g) were sequentially added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5.0 g) in THF (20 mL) and ethanol (5 mL), and the reaction solution was stirred at room temperature for nine hours. A 2 N sodium hydroxide solution (20 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was cooled to 0° C., and 2 N hydrochloric acid (20 mL) was added to the reaction solution. The resulting precipitate was collected by filtration. The resulting precipitate was washed with water and ethyl acetate to obtain 5.1 g of the title compound. The property values of the compound are as follows.
Workup
- stirringthe reaction solution was stirred at room temperature for 12 hours
- temperatureThe reaction solution was cooled to 0° C.
- filtrationThe resulting precipitate was collected by filtration
- washThe resulting precipitate was washed with water and ethyl acetate
Sources & evidence
- ORD record
- ord-106304376a4246dca60e47037f708507
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973033B2
Reaction notes
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