Tetrahydrofuran → 6-Fluoro-5-methylpyridin-3-ol
Reaction equation
O.OO.[O:4]1CCCC1.[F:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13](B(O)O)=[CH:12][N:11]=1>O>[F:9][C:10]1[N:11]=[CH:12][C:13]([OH:4])=[CH:14][C:15]=1[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrogen peroxide water (4.37 ml, 42.8 mmol) was added to a tetrahydrofuran solution (50 ml) of 2-fluoro-3-methylpyridine-5-boronic acid (5.1 g, 32.9 mmol), and stirred overnight at room temperature. Water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with aqueous 5% sodium thiosulfate solution and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 6-fluoro-5-methylpyridin-3-ol (4.03 g, yield: 96%) as a pale yellow solid.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with aqueous 5% sodium thiosulfate solution and saturated saline water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c132c5997e2244ff9e51b0e267c433e3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846700B2
Reaction notes
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