Acetic Acid → 5-([4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione

HRID 1595528ノート

反応式

HRID 1595528 の反応式
[CH3:1][CH:2]([S:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH:21]=[C:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:3].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[CH3:3][CH:2]([S:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:5])[CH3:1]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 867573785-(4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

生成物 1

HCID 867573795-([4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione収率 45.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

1.2 g (2.7 mmole) 5-(4-[2-(4-(2-propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was dissolved in 250 ml ethyl acetate by heating. 6 ml acetic acid and 1 g Pd/C (5%) were added and the hydrogenation was started while the solution was warm. After 12 hours at room temperature, more of the catalyst was added. After 60 hours the reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The hydrogenation was restarted with more Pd/C (10%) and ethyl acetate. After 6 hours the reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using dichloromethane:methanol (95:5) as eluent to give 0.557 g (yield 45.9%) of the desired product.

後処理

  1. temperatureby heating
  2. temperaturewas warm
  3. additionmore of the catalyst was added
  4. filtrationAfter 60 hours the reaction mixture was filtered through celite
  5. customthe solvent was evaporated in vacuo
  6. filtrationAfter 6 hours the reaction mixture was filtered through celite
  7. customthe solvent was evaporated in vacuo
  8. customThe crude product was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-caf7adcf92dc4616b420cb6209f8c734
出典データセット
uspto-grants-2001_09
特許番号
US06288096B1

反応ノート

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