Acetone Cyanohydrin → 2-[2-Chloro-4-(methylsulfonyl)benzoyl]-4,4-dimethyl-5-phenyl-1,3-cyclohexanedione

HRID 35504

反応式

HRID 35504 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][C:16]1([CH3:30])[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][C:19](=[O:28])[CH2:18][C:17]1=[O:29].C(N(CC)CC)C.CC(C)(O)C#N>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([CH:18]1[C:17](=[O:29])[C:16]([CH3:30])([CH3:15])[CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][C:19]1=[O:28])=[O:5]

参加物

6

反応物 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 110960194,4-Dimethyl-5-phenyl-1,3-cyclohexanedioneHCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-

生成物 1

HCID 142776582-[2-Chloro-4-(methylsulfonyl)benzoyl]-4,4-dimethyl-5-phenyl-1,3-cyclohexanedione収率 30.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-Chloro-4-(methylsulfonyl)benzoyl chloride (2.3 g, 9 mmol) and 4,4-dimethyl-5-phenyl-1,3-cyclohexanedione (2.0 g, 9 mmol) were dissolved in 50 ml of acetonitrile. Triethylamine (1.8 g, 18 mmol) was added dropwise and the resulting solution was stirred at room temperature for 1 hour. Acetone cyanohydrin (0.17 g, 2 mmol) and triethylamine (1.8 g, 18 mmol) were added and the reaction mixture was stirred at room temperature for 1.5 hour. The reaction mixture was concentrated under vacuum and the residue dissolved in 100 ml of methylene chloride. The methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water. The methylene chloride solution was dried over anhydrous magnesium sulate and concentrated under vacuum, yielding 1.2 g of the desired product as a viscous oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 1.5 hour
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionthe residue dissolved in 100 ml of methylene chloride
  4. washThe methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water
  5. dry with materialThe methylene chloride solution was dried over anhydrous magnesium sulate
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-51477c7e58d44a60921bf4f83a6b5d47
出典データセット
uspto-grants-1988_08
特許番号
US04767447

関連ノート

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