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

HRID 1856211ノート

反応式

HRID 1856211 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d583b3f2cb214fc69cfed44cacba21f6
出典データセット
uspto-grants-1980_08
特許番号
US04218448

反応ノート

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