Diisopropylamine → Methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrate

HRID 1533258ノート

反応式

HRID 1533258 の反応式
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:42]1([C:48](Cl)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>O1CCCC1.CCCCCC>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH:37]([C:48]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)=[O:49])[C:38]([O:40][CH3:41])=[O:39])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

8

反応物 5

HCID 7912DiisopropylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 2724682Lithium diisopropylamideHCID 22012370Methyl 4-(2-benzyloxyphenyl)butyrateHCID 178418339Butyllithium

生成物 1

HCID 22012461Methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrate収率 48.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a dry ice-acetone bath cooled solution of lithium diisopropylamide, prepared from diisopropylamine (222 mg) and 1.61M hexane solution of n-butyllithium (1.24 ml) in tetrahydrofuran (5.6 ml), was added methyl 4-(2-benzyloxyphenyl)butyrate (284 mg) and the mixture was stirred for 30 minutes at the same temperature. Cyclohexanecarbonyl chloride (176 mg) was added. After being stirred for 30 minutes the reaction mixture was quenched by 1N hydrochloric acid solution and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with aqueous sodium bicarbonate solution and brine, and dried. The solvent was evaporated in vacuo and the residue was purified by preparative thin layer chromatography [silica gel, ether - n-hexane (1:4)] to afford methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrate (190 mg).

後処理

  1. stirringAfter being stirred for 30 minutes the reaction mixture
  2. customwas quenched by 1N hydrochloric acid solution
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with aqueous sodium bicarbonate solution and brine
  6. customdried
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by preparative thin layer chromatography [silica gel, ether - n-hexane (1:4)]

出典と根拠

ORDレコード
ord-364b144ba91943ada6c5208408dac14c
出典データセット
uspto-grants-2001_03
特許番号
US06207686B1

反応ノート

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