(3,5-Dimethylpyridin-2-yl)methanol → 3,5-Dimethylpyridine-2-carbaldehyde

HRID 1592394Notes

Reaction equation

HRID 1592394 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.CCOC(C)=O.CCCCCC>C(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 10630548(3,5-Dimethylpyridin-2-yl)methanolHCID 21226206Ethyl acetate hexane

Product 1

HCID 187316833,5-Dimethylpyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-dimethyl-pyridin-2-yl)-methanol (2.12 g, 15.45 mmol) (Weidmann, K. et al. J. Med. Chem. 1992, 35, 438-450) in CH2Cl2 (50 mL) was added MnO2 (9.41 g, 108.18 mmol) and the reaction mixture was refluxed overnight. Then it was cooled and the mixture was filtered through a layer of celite. The filtrate was concentrated to afford a brown/yellow oil. Purification by flash column chromatography on silica get using 30% EtOAc/hexane afforded 3,5-dimethyl-pyridine-2-carbaldehyde as a yellow oil (960 mg, 31% over 3 steps). 1H NMR (CDCl3) δ 2.39 (s, 3H), 2.62 (s, 3H), 7.41 (s, 1H), 8.47 (s, 1H), 10.15 (s, 1H).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThen it was cooled
  3. filtrationthe mixture was filtered through a layer of celite
  4. concentrationThe filtrate was concentrated
  5. customto afford a brown/yellow oil
  6. customPurification by flash column chromatography on silica
  7. customget

Sources & evidence

ORD record
ord-c9ee298273fa494da1a2258a400bab1d
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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