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

HRID 1357200노트

반응식

HRID 1357200 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-59dca2e579904b5c93bc8e6ff225a1a9
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589984B1

반응 노트

불러오는 중…