(5-Fluoro-2-methoxypyridin-3-yl)methanol → 5-Fluoro-2-methoxynicotinaldehyde

HRID 509939Notes

Reaction equation

HRID 509939 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]=1

Participants

4

Reactant 1

HCID 44754796(5-Fluoro-2-methoxypyridin-3-yl)methanol

Product 1

HCID 226783235-Fluoro-2-methoxynicotinaldehydeYield 57%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

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

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite bed rinsed with ethyl acetate
  3. concentrationThe filtrate was concentrated under vacuum
  4. 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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