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Ethanol → ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate

HRID 967355
ノート
印刷プレビュー

反応式

HRID 967355 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:9]=2)=[CH:4][CH:3]=1.[CH2:26](O)[CH3:27].OS(O)(=O)=O.CCCCCC>CO.C(OC(=O)C)C>[CH2:26]([O:24][C:23](=[O:25])[CH2:22][CH2:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:11]=1)[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 8058HexaneHCID 1888503-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic Acid

生成物 1

HCID 11222871ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate収率 85%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoic acid (300 g, 840 mmol) and ethanol (3 L) were placed in a flask. Concentrated H2SO4 (2.4 mL, 86.4 meq.) was added with stirring. The reaction was then heated to reflux. After approximately 30 minutes, the suspension dissolved. The reaction was monitored by TLC (silica gel; hexane:ethylacetate:methanol;70:20:10). After refluxing for 9 hours, all starting material was gone and 2 liters of ethanol was removed by distillation. The remaining solution was cooled with stirring to 0° C. and seeded with known ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate. The resulting suspension was stirred at 0° C. for 30 minutes and then filtered, washed with cold ethanol (100 mL) and vacuum dried (room temperature, ca. 5 mm Hg) to give ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate (275.0 g, 85% yield) as a clean white powder (mp=80-81° C.). An additional 27.9 g of ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate was obtained as a tan powder after reducing the volume of the mother liquor to approximately 100 mL and seeding with known ethyl-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-propanoate.

後処理

  1. temperatureThe reaction was then heated to reflux
  2. dissolutionthe suspension dissolved
  3. temperatureAfter refluxing for 9 hours
  4. custom2 liters of ethanol was removed by distillation
  5. temperatureThe remaining solution was cooled
  6. stirringwith stirring to 0° C.
  7. stirringThe resulting suspension was stirred at 0° C. for 30 minutes
  8. filtrationfiltered
  9. washwashed with cold ethanol (100 mL) and vacuum
  10. customdried (room temperature, ca. 5 mm Hg)

出典と根拠

ORDレコード
ord-f93ad042aaa345419d742334949b0827
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06953860B2

反応ノート

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