Potassium Carbonate → HCID 68527487, compound
Reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][O:16]S(C)(=O)=O)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][O:16][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:13][N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methanesulfonic acid 6-(4-nitrophenoxy)-pyridin-3-ylmethyl ester (4.86 g, 15 mmol) was dissolved in DMF (250 mL), and to the resulting solution were added 4-hydroxybenzotrifluoride (2.92 g, 18 mmol) and potassium carbonate (3.11 g, 22.5 mmol). The resulting solution was stirred under a nitrogen atmosphere for 1 hour at 50° C. The reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate, and washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=80:1), to thereby yield 5.8 g of the title compound.
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- additionTo the residue was added ethyl acetate
- washwashed with a saturated sodium bicarbonate solution and brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customevaporated
- customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=80:1)
Sources & evidence
- ORD record
- ord-b686f903018c4588965e4985bad8fde5
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188277B2
Reaction notes
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