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p-Toluenesulfonic acid → 5-Methyl-2-phenyl-1-m-tolyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 413888
ノート
印刷プレビュー

反応式

HRID 413888 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[CH2:9]([O:11][C:12](=[O:26])[CH:13]([C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][C:15](=O)[CH3:16])[CH3:10].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)Cl>[CH2:9]([O:11][C:12]([C:13]1[CH:14]=[C:15]([CH3:16])[N:1]([C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:26])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 7934m-ToluidineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

生成物 1

HCID 99230435-Methyl-2-phenyl-1-m-tolyl-1H-pyrrole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

m-Toluidine (5 mmol, 0.5 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4 (sodium sulfate), the solids were separated, and the solvents evaporated under vacuum. The crude product was recrystallized from ethanol to yield the named product (m.p. 92.5° C.-94.0° C.).

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. dry with materialThe organic layer was dried over NaSO4 (sodium sulfate)
  5. customthe solids were separated
  6. customthe solvents evaporated under vacuum
  7. customThe crude product was recrystallized from ethanol

出典と根拠

ORDレコード
ord-210abc33d9694858aad349bfe1d0f800
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06569890B2

反応ノート

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