(5-Methoxypyridin-2-yl)methanol → 2-Formyl-5-methoxypyridine

HRID 254699Notes

Reaction equation

HRID 254699 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[N:7][CH:8]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[O:10])=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 12214020(5-Methoxypyridin-2-yl)methanol

Product 1

HCID 234506402-Formyl-5-methoxypyridine

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5.7 g (41 mmol) (5-methoxypyridin-2-yl)methanol in 100 mL CHCl3 was added 15 g MnO2 and the mixture heated to reflux for 2 hours, filtered, and washed with boiling CHCl3. The filtrate was washed with brine, dried over MgSO4, and concentrated in vacuo to afford 5-methoxypyridine-2-carbaldehyde as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.99 (s, 1H), 8.44 (d, J=2.4 Hz, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.3 (dd, J=8.4, 2.4 Hz, 1H), 3.95 (s, 2H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered
  4. washwashed with boiling CHCl3
  5. washThe filtrate was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfe938a85e194eb6ad4928939ac7d6f8
Source dataset
uspto-grants-2011_01
Patent number
US07875636B2

Reaction notes

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