Pyridine → 2-Methyl-3-hydroxy-4-acetyl-5-vinylpyridine

HRID 614398Notes

Reaction equation

HRID 614398 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:13]([OH:14])=[C:12]([CH:15]([OH:17])[CH3:16])[C:11]([CH:18]=[CH2:19])=[CH:10][N:9]=1>[O-2].[O-2].[O-2].[Cr+6].C(Cl)Cl>[CH3:7][C:8]1[C:13]([OH:14])=[C:12]([C:15](=[O:17])[CH3:16])[C:11]([CH:18]=[CH2:19])=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 202639212-Methyl-3-hydroxy-4-(1-hydroxyethyl)-5-vinylpyridine

Product 1

HCID 202640462-Methyl-3-hydroxy-4-acetyl-5-vinylpyridine

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 750 ml. of dry methylene chloride containing 47.5 ml. of dry pyridine was added with stirring and cooling 29.6 g. of chromium trioxide. The mixture was aged 20 minutes at room temperature and then treated with a solution of 10.96 g. of the product from Example 10, Step B, in 250 ml. of dry methylene chloride over 15 minutes. After one hour at room temperature, the reaction mixture was filtered and the residue was washed with 2 × 100 ml. of methylene chloride. The methylene chloride filtrates were extracted with 3 × 500 ml. of 5% (w/w) aqueous sodium hydroxide solution, dried over magnesium sulfate and evaporated to dryness. The residue was crystallized from hexane to give 2-methyl-3-hydroxy-4-acetyl-5-vinylpyridine.

Workup

  1. temperaturecooling 29.6 g
  2. additiontreated with a solution of 10.96 g
  3. waitAfter one hour at room temperature
  4. filtrationthe reaction mixture was filtered
  5. washthe residue was washed with 2 × 100 ml
  6. extractionThe methylene chloride filtrates were extracted with 3 × 500 ml
  7. dry with materialof 5% (w/w) aqueous sodium hydroxide solution, dried over magnesium sulfate
  8. customevaporated to dryness
  9. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-6409fe00a0df4a078faed1564a05d572
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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