Hydrochloric Acid → (4-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxyphenyl)acetic acid
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=2[O:25][CH3:26])[N:10]=1.Cl>[OH-].[K+]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[O:25][CH3:26])[N:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl (4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxyphenyl)acetate (6.19 g) was dissolved in 0.25N potassium hydroxide mixed solution (potassium hydroxide 7.01 g/methanol 125 mL/tetrahydrofuran 354 mL/distilled water 21 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was acidified by adding hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethanol-diisopropyl ether to give (4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxyphenyl)acetic acid as a white solid (5.43 g, yield 95%). melting point: 162-164° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed successively with distilled water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was recrystallized from ethanol-diisopropyl ether
Sources & evidence
- ORD record
- ord-e1c425a24e6d43aab40e616d2d836433
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
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