4-Chlorobutyryl chloride → 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid dimethylamide

HRID 1066472

反応式

HRID 1066472 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][N:13]([CH3:25])[C:14](=[O:24])[C:15]([CH3:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:25][N:13]([CH3:12])[C:14](=[O:24])[C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][Cl:5])=[CH:21][CH:22]=1)([CH3:23])[CH3:16]

参加物

6

反応物 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 540072552-Methyl-2-phenyl-propionic acid, dimethylamide

生成物 1

HCID 120498702-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid dimethylamide収率 72.4%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Add AlCl3 (1.12 g, 8.40 mmol) to carbon tetrachloride (6 mL) under a nitrogen atmosphere at room temperature. Add 4-chlorobutyryl chloride (0.49 mL, 4.37 mmol), stir for 15 minutes and add, by dropwise addition over 3 minutes, a solution of 2-methyl-2-phenyl-propionic acid, dimethylamide (0.64 g, 3.36 mmol) in carbon tetrachloride (6 mL). Stir at room temperature for 17 hours, dilute with methylene chloride (10 mL), pour into ice water (50 mL) and separate the layers. Wash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate, combine the organic layers and dry (Na2SO4). Filter, evaporate the filtrate in vacuo and purify by silica gel chromatography (5:2 hexane/ethyl acetate) to give the title compound (0.72 g, 72%) as a light yellow oil.

後処理

  1. additionadd, by dropwise addition over 3 minutes
  2. customseparate the layers
  3. washWash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate
  4. dry with materialdry (Na2SO4)
  5. filtrationFilter
  6. customevaporate the filtrate in vacuo
  7. custompurify by silica gel chromatography (5:2 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-c08956b0c7954c5889c085bc33e328ef
出典データセット
uspto-grants-2001_06
特許番号
US06242606B1

関連ノート

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