Acetone Cyanohydrin → 4-(2'-Nitro-4'-chlorobenzoyl)-2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dione

HRID 867975ノート

反応式

HRID 867975 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:14][C:15]1([CH3:23])[C:20](=[O:21])[CH2:19][C:18](=[O:22])[CH2:17][O:16]1.C(N(CC)CC)C.CC(C)(O)C#N>[Cl-]>[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([CH:19]1[C:18](=[O:22])[CH2:17][O:16][C:15]([CH3:23])([CH3:14])[C:20]1=[O:21])=[O:7])([O-:3])=[O:2]

参加物

6

反応物 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 140728872,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

生成物 1

HCID 140728884-(2'-Nitro-4'-chlorobenzoyl)-2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dione収率 43%

試薬・触媒・溶媒 1

HCID 312Chloride溶媒

実験手順

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and, 2,2-dimethyl-2H-pyran-3,5-(4H,6H)-dione (1.4 g, 10 mmol) were dissolved in 150 milliliters (ml) chloride. Triethylamine (3 ml, 22 mmol) was added and the resulting solution stirred at room temperature for fifteen minutes. The solution was washed with dilute hydrochloric acid, 5% potassium carbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was dissolved in 10 ml acetonitrile. Triethylamine (3 ml, 22 mmol) and acetone cyanohydrin (0.2 g) were added and the mixture stirred at room temperature for 2 hours. After dilution with either, the solution was washed with dilute hydrochloric acid and extracted with 5% potassium carbonate. The basic extract was acidified with hydrochloric acid and extracted with ether. The ether extract was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under vacuum, yielding 1.4 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. washThe solution was washed with dilute hydrochloric acid, 5% potassium carbonate and saturated sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 10 ml acetonitrile
  5. stirringthe mixture stirred at room temperature for 2 hours
  6. washAfter dilution with either, the solution was washed with dilute hydrochloric acid
  7. extractionextracted with 5% potassium carbonate
  8. extractionThe basic extract
  9. extractionextracted with ether
  10. extractionThe ether extract
  11. washwas washed with saturated sodium chloride
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-24dbd9a4d8d84ff9909119a9d2bc5729
出典データセット
uspto-grants-1988_10
特許番号
US04777272

反応ノート

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