Dimethyl Sulfoxide → Ethyl (3-fluoro-2-pyridyl)acetate
Reaction equation
[F:1][C:2]1[C:3]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.CS(C)=O.[Cl-].[Na+]>O>[F:1][C:2]1[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 148.5 °C
Procedure
5.10 g of diethyl (3-fluoro-2-pyridyl)malonate and 25 ml of dimethyl sulfoxide were mixed. To the mixture was added 1.29 g of sodium chloride and 0.72 g of water. The mixture was stirred for about 40 minutes at an inner temperature of 145 to 152° C. The reaction mixture was allowed to cool to room temperature, then, to the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure, to obtain 2.99 g of ethyl (3-fluoro-2-pyridyl)acetate.
Workup
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine twice
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0a983c8d24f74292a83c85937acc932f
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598176B2
Reaction notes
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