Sodium Hydroxide → 1-Phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione

HRID 1725184

反応式

HRID 1725184 の反応式
C(OC(=O)[CH:5]([C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]1)=[O:16])[CH2:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[C:8]1([C:7](=[O:14])[CH2:6][CH2:5][C:15]([CH:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21][CH2:22]2)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 690616894-Oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester

生成物 1

HCID 574237211-Phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione収率 23.6%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 7.63 g (21.3 mmol) 4-oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester in 66 mL toluene was added 36 mL 3M aqueous sodium hydroxide and 0.32 g (0.96 mmol) tetra-n-butylammonium hydrogen sulfate. The reaction was heated to reflux over 16 hr, allowed to cool and poured into brine. The solution was extracted two times with ether and concentrated to give an oil. The crude product was chromatographed on silica to give 1.44 g 1-phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione as a red solid.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux over 16 hr
  3. temperatureto cool
  4. extractionThe solution was extracted two times with ether
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude product was chromatographed on silica

出典と根拠

ORDレコード
ord-2775bc07a7644e7a8c9e824f089b1ddc
出典データセット
uspto-grants-2009_02
特許番号
US07488832B2

関連ノート

読み込み中…