Tetrahydrofuran → 6-Fluoro-5-methylpyridin-3-ol

HRID 1517287Notes

Reaction equation

HRID 1517287 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

HCID 8028TetrahydrofuranHCID 449047Hydrogen peroxide waterHCID 17750247(6-Fluoro-5-methylpyridin-3-yl)boronic acid

Product 1

HCID 229897166-Fluoro-5-methylpyridin-3-olYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous 5% sodium thiosulfate solution and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8e9a31285f1488e942a777094ac20da
Source dataset
uspto-grants-2012_07
Patent number
US08232284B2

Reaction notes

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