Thiazolidinedione → 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinylidene)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one

HRID 1357200ノート

反応式

HRID 1357200 の反応式
N1CCCCC1.C([O:10][C:11]1[C:16]([CH3:17])=[C:15]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][C:21]=3[CH:22]=2)[O:14][C:13](=[O:29])[C:12]=1[CH3:30])(=O)C.[S:31]1[CH2:35][C:34](=[O:36])[NH:33][C:32]1=[O:37].[OH-].[Na+]>C1COCC1>[CH3:30][C:12]1[C:13](=[O:29])[O:14][C:15]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][C:24]([CH:27]=[C:35]4[C:34](=[O:36])[NH:33][C:32](=[O:37])[S:31]4)=[CH:23][C:21]=3[CH:22]=2)=[C:16]([CH3:17])[C:11]=1[OH:10]

参加物

6

反応物 4

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 154628324-acetyloxy-3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-2H-pyran-2-one

生成物 1

HCID 547366073,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinylidene)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Piperidine (100 mg) was added to a solution of 4-acetyloxy-3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-2H-pyran-2-one (374 mg) and 1,3-thiazolidine-2,4-dione (135 mg) in THF (50 ml), and the mixture was subjected to heated reflux for 4 hours. After cooling, a 15% sodium hydroxide aqueous solution (10 ml) was added to the reaction solution, and then after stirring for one hour it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH=5/1) to obtain 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinylidene)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one.

後処理

  1. temperatureto heated
  2. temperaturereflux for 4 hours
  3. temperatureAfter cooling
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=5/1)

出典と根拠

ORDレコード
ord-59dca2e579904b5c93bc8e6ff225a1a9
出典データセット
uspto-grants-2003_07
特許番号
US06589984B1

反応ノート

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