Hydrochloric Acid → (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1)[CH:6]=O.C([O:19][C:20](=[O:30])[CH2:21]P(OCC)(OCC)=O)C.O.[OH-].[Li+].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:21]/[C:20]([OH:30])=[O:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a THF (40 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (4.00 g) obtained in Example 1, diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added one by one, and the reaction solution was agitated overnight at room temperature. 2N sodium hydroxide solution (30 mL) and ethanol (5 mL) were added to the reaction solution after confirming disappearance of the starting materials, and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0° C., 2N hydrochloric acid (30 mL) was added to the reaction solution, and the precipitation consequently deposited was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.61 g of the title compound was obtained. The physical properties of the compound are as follows.
Workup
- stirringthe reaction solution was agitated at room temperature overnight
- temperatureThe reaction solution was cooled to 0° C.
- customthe precipitation
- customconsequently deposited was separated
- filtrationby filtering with Kiriyama funnel
- customThe obtained precipitation
- washwas washed with water and ethyl acetate
Sources & evidence
- ORD record
- ord-0e475d85b1d047d1869d81f265c6c992
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07667041B2
Reaction notes
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