4-Methylpyridine → HCID 5375544, compound

HRID 355391Notes

Reaction equation

HRID 355391 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[F:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:7]/[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 5375544HCID 5375544, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 4-picoline (15.6 ml, 161 mmol) and 4-fluorobenzaldehyde (20 g, 161 mmol) in acetic anhydride (125 ml) was heated at reflux overnight. The reaction was cooled and the solvent evaporated. Water (100 ml) was added to the residue, and the mixture stirred at room temperature for 30 minutes. Saturated sodium carbonate solution (100 ml) and ethyl acetate (150 ml) were then added, and stirring continued for a further 30 minutes. The two phases were separated, and the aqueous phase extracted with ethyl acetate (3×200 ml). The combined organic phases were dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting with 50% ethyl acetate/petrol (60°-80°). The appropriate fractions were combined and concentrated to yield (E)-4-[2-(4-fluorophenyl)ethenyl]pyridine (19 g, 60%) as a beige solid. δH (CDCl3) 6.93 (1H, d, J 16.3 Hz, ArCHCH), 7.05-7.13 (2H, m, ArH), 7.26 (1H, d, J 16.3 Hz, ArCHCH), 7.34-7.36 (2H, m, ArH), 7.48-7.54 (2H, m, ArH) and 8.56-8.60 (2H, m, ArH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated
  5. additionWater (100 ml) was added to the residue
  6. additionSaturated sodium carbonate solution (100 ml) and ethyl acetate (150 ml) were then added
  7. stirringstirring
  8. waitcontinued for a further 30 minutes
  9. customThe two phases were separated
  10. extractionthe aqueous phase extracted with ethyl acetate (3×200 ml)
  11. dry with materialThe combined organic phases were dried (MgSO4)
  12. customevaporated
  13. customThe residue was purified by flash chromatography
  14. washeluting with 50% ethyl acetate/petrol (60°-80°)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-7f4dd79779c448579ec9f88d59f05c1d
Source dataset
uspto-grants-1998_11
Patent number
US05830901

Reaction notes

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