Methyl iodide → Methyl 2-(4-chlorophenyl)-2-cyclopentylpropanoate

HRID 12299ノート

反応式

HRID 12299 の反応式
[CH:1](NC(C)C)(C)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1.CI>C1COCC1.C([Li])CCC.[Cl-].[NH4+]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)([CH3:1])[C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 23092013Methyl 2-(4-chlorophenyl)-2-cyclopentylacetate

生成物 1

HCID 23092040Methyl 2-(4-chlorophenyl)-2-cyclopentylpropanoate

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 25517Ammonium Chloride溶媒HCID 178418339Butyllithium溶媒

反応条件

温度
-35 °C

実験手順

To a solution of diisopropylamine (0.15 ml) in THF (2 ml), n-butyl lithium (1.5 M hexane solution, 0.6 ml) was added at −78° C., stirred for 10 minutes and another solution of methyl 2-(4-chlorophenyl)-2-cyclopentylacetate (200 mg) in THF (1.5 ml) was added dropwise. After 15 minutes' stirring, the system temperature was raised to −35° C., and methyl iodide (0.15 ml) was added. The reaction liquid temperature was raised to 0° C., and the liquid was stirred for 1.5 hours, diluted with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure. The resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1) to provide methyl 2-(4-chlorophenyl)-2-cyclopentylpropionate (180 mg) as yellow oily substance.

後処理

  1. stirringAfter 15 minutes' stirring
  2. customThe reaction liquid temperature
  3. temperaturewas raised to 0° C.
  4. stirringthe liquid was stirred for 1.5 hours
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate and condensed under reduced pressure
  8. customThe resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1)

出典と根拠

ORDレコード
ord-605b849843804862a90b8e36f41a45f4
出典データセット
uspto-grants-2010_06
特許番号
US07727998B2

反応ノート

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