Water → 2,3-Bis(4-fluorophenyl)-1-methyl-5-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]-1H-pyrrole

HRID 2412953Notes

Reaction equation

HRID 2412953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])O)[NH: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.[C:30](=[O:33])([O-])[O-].[K+].[K+].[CH3:36]I.O>CN(C=O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]([CH3:36])[C:10]([C:20]([O:33][CH3:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:9][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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 12831594HCID 12831594, compound

Product 1

HCID 133713622,3-Bis(4-fluorophenyl)-1-methyl-5-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]-1H-pyrroleYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.1 g (0.005 mole) of 4,5bis(4-fluorophenyl)-α,α-bis(trifluoromethyl)-1H-pyrrole-2-methanol, 1.4 g anhydrous potassium carbonate and 0.9 g (0.006 mole) of methyl iodide in 25 ml DMF was stirred at room temperature overnight. Another 1.4 g of potassium carbonate and 0.3 g of methyl iodide was added and stirring was continued another two hours. The mixture was poured into water and extracted with ether. The ether layers were backwashed with water three times, then dried and concentrated. The residue was purified by chromatography on silica gel, eluting with hexane/toluene (90/10) to give 1.7 g of the O,N-dimethylated product, m.p. 133°-134° (from ethanol/water). The infrared and nmr spectrum were consistent with the structure.

Workup

  1. stirringstirring
  2. waitwas continued another two hours
  3. extractionextracted with ether
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with hexane/toluene (90/10)

Sources & evidence

ORD record
ord-35b21a164286499684f63a63877c5d37
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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