4-Pyridinecarboxaldehyde → 2-Furyl-3-(4-pyridyl)-2-propene-1-one

HRID 1440712Notes

Reaction equation

HRID 1440712 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:9]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)(=[O:11])[CH3:10]>CN(C)C=O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:9](=[O:11])[CH:10]=[CH:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 145052-Acetylfuran

Product 1

HCID 4663252-Furyl-3-(4-pyridyl)-2-propene-1-oneYield 0.3%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve anhydrous cobalt(II) acetate (700 mg, 4 mmol ) in dimethylformamide (150 mL). Add 2,2'-dipyridyl (600 mg, 4 mmol) and stir for 30 minutes. Add 4-pyridinecarboxaldehyde (5 g, 50 mmol) and 2-acetylfuran (5.5 g, 50 mmol). Heat at 80° C. for 18 hours. Evaporate the solvent and purify the residue by silica gel chromatography (1:1 toluene/ethyl acetate) to yield 30 mg of the title compound; mp 122°-124° C.

Workup

  1. customEvaporate the solvent
  2. custompurify the residue by silica gel chromatography (1:1 toluene/ethyl acetate)

Sources & evidence

ORD record
ord-a68e65ec1e4e48cb8affa02ebb6e0fb6
Source dataset
uspto-grants-1996_03
Patent number
US05500429

Reaction notes

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