Methanol → 6-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-1,4,8-trimethyl-2(1H)-quinolinone

HRID 1856211Notes

Reaction equation

HRID 1856211 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([CH3:26])[CH:25]=1)[NH:22][C:21](=[O:27])[CH:20]=[C:19]2[CH3:28])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].[O-][CH2:32]C.[Tl+].CI.CO>CN(C)C=O>[F:30][C:2]([F:1])([F:29])[C:3]([C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([CH3:26])[CH:25]=1)[N:22]([CH3:32])[C:21](=[O:27])[CH:20]=[C:19]2[CH3:28])([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 30143Ethanol, thallium(1+) saltHCID 233461046-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-4,8-dimethyl-2(1H)-quinolinone

Product 1

HCID 233461336-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-1,4,8-trimethyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-4,8-dimethyl-2(1H)-quinolinone in dimethylformamide is added an equivalent of thallium ethoxide. The solution is stirred under nitrogen. To the solution is added methyl iodide, and the solution is stirred and heated to 50° until thin layer chromatography indicates the reaction is complete. The solution is cooled and treated with 5 ml of methanol. The cooled solution is filtered and evaporated at reduced pressure. The residual material is extracted with hexane and the filtered solution is evaporated at reduced pressure. The residual material is heated to 250° in a nitrogen atmosphere for 4 hours. At the end of this period, the residual material is chromatographed on silicic acid to give 6-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-1,4,8-trimethyl-2(1H)-quinolinone.

Workup

  1. stirringthe solution is stirred
  2. temperatureheated to 50° until thin layer chromatography
  3. temperatureThe solution is cooled
  4. filtrationThe cooled solution is filtered
  5. customevaporated at reduced pressure
  6. extractionThe residual material is extracted with hexane
  7. customthe filtered solution is evaporated at reduced pressure
  8. temperatureThe residual material is heated to 250° in a nitrogen atmosphere for 4 hours
  9. customAt the end of this period, the residual material is chromatographed on silicic acid

Sources & evidence

ORD record
ord-d583b3f2cb214fc69cfed44cacba21f6
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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