Water → 4-Allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carboxylic Acid
Reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:12]2[C:13]([C:17]([OH:19])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[OH:20])=[O:6])[CH:2]=[CH2:3].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)C=1.C(=O)([O-])[O-].[K+].[K+].O.C[N:43](C)C=O>>[CH2:1]([O:4][C:5]([C:7]1[C:12]2[C:13]([C:17]([OH:19])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[O:20][C:25]1[N:43]=[C:23]([O:22][CH3:21])[CH:28]=[C:27]([O:29][CH3:30])[N:26]=1)=[O:6])[CH:2]=[CH2:3]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
A mixture comprising 54.2 g of 4-allyloxycarbonyl-5-hydroxy-2-methylbenzofuran-3-carboxylic acid, 47 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 65 g of potassium carbonate in 200 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, and then the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Crystals obtained by concentration under reduced pressure, were washed with isopropyl ether to obtain 79.2 g (yield: 98%) of the desired compound.
Workup
- temperaturewas heated
- customwas returned to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customCrystals obtained by concentration under reduced pressure
- washwere washed with isopropyl ether
Sources & evidence
- ORD record
- ord-c317843f65ba47bebddd862b2745b9a7
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616537
Reaction notes
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