2,6-Dimethyl-4-(hydroxymethyl)pyridine → 2,6-Dimethylpyridine-4-carbaldehyde

HRID 591819Notes

Reaction equation

HRID 591819 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1>CS(C)=O>[CH3:10][C:5]1[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=[C:7]([CH3:9])[N:6]=1

Participants

3

Reactant 1

HCID 38250772,6-Dimethyl-4-(hydroxymethyl)pyridine

Product 1

HCID 27630042,6-Dimethylpyridine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Hydroxymethyl-2,6-dimethylpyridine (24.7 g, 180 mmol, 1.0 equiv.) was dissolved in DMSO (200 mL), and IBX (53.0 g, 189 mmol, 1.05 equiv.) was added in portions, the mixture was stirred at room temperature for 2 hours; TLC indicated complete reaction. The mixture was filtered, washed with water and ether. The filtrate was extracted with ether (4×150 mL); the combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was purified by column chromatography (20% ether in hexanes as eluent) to give 2,6-dimethyl-4-pyridinecarboxaldehyde as a yellow oil. Yield: 20.0 g (82%).

Workup

  1. additionIBX (53.0 g, 189 mmol, 1.05 equiv.) was added in portions
  2. customreaction
  3. filtrationThe mixture was filtered
  4. washwashed with water and ether
  5. extractionThe filtrate was extracted with ether (4×150 mL)
  6. washthe combined extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by column chromatography (20% ether in hexanes as eluent)

Sources & evidence

ORD record
ord-fa8a96c0e77243878b66d04ee82b668c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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