Ethyl Acetate → HCID 21705014, compound

HRID 1595490Notes

Reaction equation

HRID 1595490 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][C:22]3[CH:35]=[CH:34][C:25]([CH:26]=[C:27]4[S:31][C:30](=[O:32])[NH:29][C:28]4=[O:33])=[CH:24][CH:23]=3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(OCC)(=O)C>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][C:22]3[CH:35]=[CH:34][C:25]([CH2:26][CH:27]4[S:31][C:30](=[O:32])[NH:29][C:28]4=[O:33])=[CH:24][CH:23]=3)=[CH:17][CH:18]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 54432062HCID 54432062, compound

Product 1

HCID 21705014HCID 21705014, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.2 g (2.35 mmole) 5-(4-[2-(4-(4-methoxyphenylsulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was mixed with 200 ml warm ethyl acetate, 2 ml acetic acid and 1.2 g Pd/C (5%, 50% water) and hydrogenated for 4 hours at room temperature. 1.2 g more of the catalyst was added after 2 hours. The catalyst was filtered off and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using dichloromethane/diisopropyl ether (gradient) as eluent to give 0.5 g of the desired product.

Workup

  1. addition1.2 g more of the catalyst was added after 2 hours
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated in vacuo
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-afe2698f26004906b07bc0051118378a
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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