Furan → 2-(2-Furanyl)-6-methylpyridine

HRID 376277Notes

Reaction equation

HRID 376277 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH3:11][C:12]1[N:17]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:15]=[CH:14][CH:13]=1>CCCCCC.O1CCCC1.[Cl-].[Cl-].[Zn+2]>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:11])[N:17]=1

Participants

7

Reactant 3

HCID 8029FuranHCID 10847672HCID 10847672, compoundHCID 178418339Butyllithium

Product 1

HCID 193617452-(2-Furanyl)-6-methylpyridineYield 81.5%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

40 ml of a 1.6 M solution of n-butyllithium in hexane are introduced dropwise into a solution of 4.36 ml of furan (60 mmol) and 40 ml of tetrahydrofuran cooled to 0° C. The solution is stirred for 3 hours at 0° C. and then it is cooled to -40° C. before introducing 120 ml of a 0.5 M solution of zinc dichloride in tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and then the reaction mixture is added to a solution of 9.17 g of trifluoromethanesulfonic acid 6-methylpyridin-2-yl ester (40 mmol) in 20 ml of tetrahydrofuran containing 2.30 g of tetrakis-(triphenylphosphine)palladium (2 mmol). The reaction mixture is maintained under reflux for 2 hours under nitrogen and then cooled and extracted with 1N HCl. The acidic aqueous phase is neutralized with 10N NaOH and then extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and the solvent evaporated off. The expected product is isolated by rectification under reduced pressure.

Workup

  1. temperatureit is cooled to -40° C.
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. temperatureThe reaction mixture is maintained
  4. temperatureunder reflux for 2 hours under nitrogen
  5. temperaturecooled
  6. extractionextracted with 1N HCl
  7. extractionextracted with ethyl acetate
  8. washThe organic phase is washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent evaporated off

Sources & evidence

ORD record
ord-93fc0c56b937438a86878fc53e39b615
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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