(5-Fluoro-2-methoxypyridin-3-yl)methanol → 5-Fluoro-2-methoxynicotinaldehyde
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1>C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To (5-fluoro-2-methoxy-pyridin-3-yl)-methanol (36, 8 g, 50.9 mmol) in 300 mL of ethyl acetate, manganese(IV) oxide (39.8 g, 458 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was filtered through celite, and the celite bed rinsed with ethyl acetate. The filtrate was concentrated under vacuum, then passed through a plug of silica, eluting with 50% ethyl acetate in heptane to provide the desired compound as a light yellow solid (37, 4.5 g, 29.0 mmol, 57.0% yield).
Workup
- filtrationThe reaction mixture was filtered through celite
- washthe celite bed rinsed with ethyl acetate
- concentrationThe filtrate was concentrated under vacuum
- washeluting with 50% ethyl acetate in heptane
Sources & evidence
- ORD record
- ord-973f28eabc2548f0814f563d2ede27d0
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096593B2
Reaction notes
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