Potassium Carbonate → HCID 18472396, compound
Reaction equation
[N+:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[O:14][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
In DMF (50 ml) was dissolved methyl 5-nitrosalicylate (1.97 g, 10.0 mmol), and to the mixture were added ethyl 4-bromobutyrate (1.57 ml, 11.0 mmol) and potassium carbonate (2.76 g, 20.0 mmol). The mixture was stirred at 110° C. for 5 hours, and the mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed with water and 10% potassium carbonate solution. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/5→1/3), and the desired fraction was concentrated under reduced pressure to give ethyl 4-(2-methoxycarbonyl-4-nitrophenoxy)butyrate (2.51 g, 8.06 mmol, 81%).
Workup
- concentrationthe mixture was concentrated under reduced pressure
- additionTo the residue was added ethyl acetate
- washthe mixture was washed with water and 10% potassium carbonate solution
- dry with materialThe organic layer was dried with anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/5→1/3)
- concentrationthe desired fraction was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9b17d9c199474c78aba07847286cdc01
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06413947B1
Reaction notes
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