Hexafluoroacetone trihydrate → 4,5-Bis(4-fluorophenyl)-1-methyl-alpha,alpha-bis(trifluoromethyl)-1H-pyrrole-2-methanol

HRID 2412950Notes

Reaction equation

HRID 2412950 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:20])[CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.O.O.O.[F:24][C:25]([F:33])([F:32])[C:26]([C:28]([F:31])([F:30])[F:29])=[O:27]>C1(C)C=CC=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[CH:11]=[C:10]([C:26]([C:28]([F:31])([F:30])[F:29])([C:25]([F:33])([F:32])[F:24])[OH:27])[N:9]([CH3:20])[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 36719Hexafluoroacetone trihydrate3×HCID 128733522,3-bis(4-fluorophenyl)-1-methyl-1H-pyrrole

Product 1

HCID 133713504,5-Bis(4-fluorophenyl)-1-methyl-alpha,alpha-bis(trifluoromethyl)-1H-pyrrole-2-methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.0 g (0.015 mole) of 2,3-bis(4-fluorophenyl)-1-methyl-1H-pyrrole and 3.7 g (0.017 mole) of hexafluoroacetone trihydrate in 75 ml toluene was heated at reflux overnight. Another 3.7 g of hexafluoroacetone trihydrate was added and the mixture was heated at reflux overnight again. An additional 2.0 g of hexafluoroacetone trihydrate was added and the mixture was heated at reflux another eight hours. The mixture was washed twice with water, then the organic layer was dried and concentrated. The crude product was purified by chromatography on silica gel, eluting with hexane/toluene mixtures to give, after recrystallization from hexane, 4.8 g of product, m.p. 130°-131°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture was heated
  4. temperatureat reflux overnight again
  5. temperaturethe mixture was heated
  6. temperatureat reflux another eight hours
  7. washThe mixture was washed twice with water
  8. customthe organic layer was dried
  9. concentrationconcentrated
  10. customThe crude product was purified by chromatography on silica gel
  11. washeluting with hexane/toluene
  12. customto give
  13. customafter recrystallization from hexane, 4.8 g of product, m.p. 130°-131°

Sources & evidence

ORD record
ord-2c5894ee05764e50a7baa2b12a99547b
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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