2-Acetylthiophene → 1-(Thiophen-2-yl)-3-(4-pyridinyl)-2-propene-1-one

HRID 1440713Notes

Reaction equation

HRID 1440713 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[N:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1>CN(C)C=O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[S:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:1](=[O:3])[CH:2]=[CH:15][C:12]1[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 69202-AcetylthiopheneHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 539330401-(Thiophen-2-yl)-3-(4-pyridinyl)-2-propene-1-oneYield 1.1%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Dissolve anhydrous cobalt(II) acetate (700 mg, 4 mmol) in dimethylformamide (100 mL) . Add 2,2'-dipyridyl (600 mg, 4 mmol) and stir for 30 minutes. Add 2-acetylthiophene (6.3 g, 50 mmol) and 4-pyridinecarboxaldehyde (5 g, 50 mmol) and heat at 80° C. for 18 hours. Evaporate the solvent and purify the resiude by silica gel chromatography (1:1 toluene/ethyl acetate). Recrystallize (ethyl ether/hexane) to yield 120 mg of the title compound; mp 150.5°-152° C.

Workup

  1. customEvaporate the solvent
  2. custompurify the resiude by silica gel chromatography (1:1 toluene/ethyl acetate)
  3. customRecrystallize (ethyl ether/hexane)

Sources & evidence

ORD record
ord-a1629b9511cf40dcbbf979351fb92849
Source dataset
uspto-grants-1996_03
Patent number
US05500429

Reaction notes

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