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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
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HRID 2037178 반응식
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]
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참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc4b6fe35cc742499ecf0cff7786da40
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575197B2

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