1,1,1-Trifluoro-2,4-pentanedione → 1-(4-Methoxyphenyl)-5-methyl-3-(trifluoromethyl)-1H-pyrazole

HRID 394769Notes

Reaction equation

HRID 394769 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3](=O)[CH2:4][C:5](=O)[CH3:6].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.Cl>COCCO.C(O)(=O)C>[F:1][C:2]([F:10])([F:9])[C:3]1[CH:4]=[C:5]([CH3:6])[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[N:20]=1

Participants

5

Reactant 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 181772961-(4-Methoxyphenyl)-5-methyl-3-(trifluoromethyl)-1H-pyrazoleYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1,1,1-trifluoro-2,4-pentanedione (0.02 mol, 2.4 mL) and 4-methoxyphenyl hydrazine.HCl (4.54 g, 1.3 eq.) in 2-methoxyethanol (100 mL) and acetic acid (30 mL) was refluxed for 6 h. The reaction mixture was evaporated and purified by flash chromatography on a silica gel column (400 g) eluted with 4:1 hexane:ethyl acetate to give 4.5 g of pure product (88%).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe reaction mixture was evaporated
  3. custompurified by flash chromatography on a silica gel column (400 g)
  4. washeluted with 4:1 hexane

Sources & evidence

ORD record
ord-ef898be4e270474d8802bbe2da8bf558
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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