4-Pyridinecarboxaldehyde → 3-(Pyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one

HRID 1440711Notes

Reaction equation

HRID 1440711 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:3].[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1>CN(C)C=O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[F:13][C:10]([F:11])([F:12])[C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:20][C:17]2[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 536609773-(Pyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve anhydrous cobalt(II) acetate (700 mg, 4 mmol) in dimethylformamide. Add 2,2'-dipyridyl (620 mg, 4 mmol) and stir for 30 minutes. Add 3-(trifluoromethyl)acetophenone (9.4 g, 50 mmol) and 4-pyridinecarboxaldehyde (5.3 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 9.4 g. Recrystallize (ethyl ether/hexane) to yield the title compound; mp 89°-90° C.

Workup

  1. customEvaporate the solvent
  2. custompurify the residue by silica gel chromatography (1:1 toluene/ethyl acetate)
  3. customto yield 9.4 g
  4. customRecrystallize (ethyl ether/hexane)

Sources & evidence

ORD record
ord-e90b6eb1b00f4047b8d5645207ce3836
Source dataset
uspto-grants-1996_03
Patent number
US05500429

Reaction notes

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