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Acetic Acid → 4-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

HRID 2037178
ノート
印刷プレビュー

反応式

HRID 2037178 の反応式
CCO[C:4]([C:6]([CH2:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[O:7])=[O:5].[S:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)=[CH:16]1.[CH3:27][O:28][C:29]([CH2:31][O:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O)=[O:30].C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.O1CCOCC1>[CH3:14][C:11]([CH3:12])([CH3:13])[C:9]([C:8]1[CH:35]([C:34]2[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=2[O:32][CH2:31][C:29]([O:28][CH3:27])=[O:30])[N:24]([C:23]2[CH:25]=[CH:26][C:20]([C:17]3[CH:18]=[CH:19][S:15][CH:16]=3)=[CH:21][CH:22]=2)[C:4](=[O:5])[C:6]=1[OH:7])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 176Acetic AcidHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoateHCID 516892Sodium BicarbonateHCID 41303364-(Thiophen-3-yl)anilineHCID 5151625Methyl 2-(2-formylphenoxy)acetate

生成物 1

HCID 583653294-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one
収率 41.5%

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of ethyl trimethylacetopyruvate (0.40 g, 2 mmol), 4-thiophene-3-ylaniline (0.35 g, 2 mmol), 2-(methoxycarbonylmethyloxy)benzaldehyde (0.39, 2 mmol), acetic acid (0.057 mL, 1 mmol) and dioxane (4 mL) was heated at reflux overnight. After the reaction was completed, saturated sodium bicarbonate solution and brine were poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulphate, and then concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform), and the aimed compound was triturated with ethyl acetate and diisopropyl ether to give 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.42 g, yield: 41%) as pale brown solid.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)
  7. customthe aimed compound was triturated with ethyl acetate and diisopropyl ether

出典と根拠

ORDレコード
ord-fc4b6fe35cc742499ecf0cff7786da40
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575197B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート