Methyl iodide → Methyl 1-(4-fluorophenyl)-4-oxocyclohexane-1-carboxylate

HRID 1065264ノート

反応式

HRID 1065264 の反応式
[CH3:1][O-].[Na+].[Na].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:19]([OH:21])=[O:20])[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.IC>CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:19]([O:21][CH3:1])=[O:20])[CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17]2)=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

生成物 1

HCID 20540244Methyl 1-(4-fluorophenyl)-4-oxocyclohexane-1-carboxylate収率 36%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred sodium methoxide solution, previously prepared starting from 1.3 parts of sodium in 160 parts of methanol, are added 13 parts of 1-(4-fluorophenyl)-4-oxocyclohexanecarboxylic acid and the whole is stirred and refluxed for 1 hour. After cooling to room temperature, 22.8 parts of iodomethane are added dropwise. Upon completion, the whole is heated to reflux and stirring is continued overnight at reflux temperature. The reaction mixture is evaporated and the residue is taken up in trichloromethane. The organic phase is washed successively with water, a 5% sodium hydroxide solution and again with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5 parts (36%) of methyl 1-(4-fluorophenyl)-4-oxocyclohexanecarboxylate as an oily residue.

後処理

  1. temperaturerefluxed for 1 hour
  2. temperatureUpon completion, the whole is heated
  3. temperatureto reflux
  4. stirringstirring
  5. temperatureat reflux temperature
  6. customThe reaction mixture is evaporated
  7. washThe organic phase is washed successively with water
  8. dry with materiala 5% sodium hydroxide solution and again with water, dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by column-chromatography over silica gel
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

出典と根拠

ORDレコード
ord-38035ee2605541f28c7ce94a77de033b
出典データセット
uspto-grants-1982_05
特許番号
US04329353

反応ノート

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