Ethyl Acetoacetate → HCID 69205750、化合物

HRID 30620ノート

反応式

HRID 30620 の反応式
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[NH2:9])=O)=[CH:4][CH:3]=1.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=O>C(O)C>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]2[N:8]([CH3:10])[N:9]=[C:15]([CH3:17])[C:14]=2[C:13]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 8868Ethyl AcetoacetateHCID 450757084-Fluorobenzoic acid N-methylhydrazide

生成物 1

HCID 69205750HCID 69205750、化合物収率 44%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-fluoro-N-methylbenzohydrazide (5.0 g), ethyl acetoacetate (4.84 g) and ethanol (140 ml) was stirred for 14 hrs. with heating under reflux. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with hexane-ethyl acetate (4:1-1:1, v/v). This oil was dissolved in ethanol (50 ml), 1,8-diazabicyclo[5.4.0]-7-undecene (0.5 ml) was added, and the mixture was stirred for 4 hrs. with heating under reflux. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give ethyl 5-(4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate (3.41 g, yield 44%) as colorless crystals.

後処理

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give an oil from a fraction
  10. washeluted with hexane-ethyl acetate (4:1-1:1
  11. dissolutionThis oil was dissolved in ethanol (50 ml)
  12. addition1,8-diazabicyclo[5.4.0]-7-undecene (0.5 ml) was added
  13. stirringthe mixture was stirred for 4 hrs
  14. temperaturewith heating
  15. temperatureunder reflux
  16. additionWater was added to the reaction mixture
  17. extractionthe mixture was extracted with ethyl acetate
  18. washThe organic layer was washed with water
  19. dry with materialdried over anhydrous magnesium sulfate
  20. concentrationconcentrated

出典と根拠

ORDレコード
ord-5dd5c739e64f4e12a9259ec84e2ff7af
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

読み込み中…