Tetrahydrofuran → HCID 11118078, compound

HRID 1581649Notes

Reaction equation

HRID 1581649 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:5][CH:4]=1.O1CCCC1>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 2331125-(4-Methoxybenzylidene)-thiazolidine-2,4-dione

Product 1

HCID 11118078HCID 11118078, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-[(4-Methoxyphenyl)methylidene]thiazolidine-2,4-dione (6.00 g, 25.5 mmol), 10% palladium on carbon (6.00 g) and a mixed solvent of tetrahydrofuran and ethanol (2:1 v/v, 300 mL) were mixed, and hydrogenation was performed at room temperature and at an initial pressure of 294 kPa. After completion of the reaction, catalyst was filtered and the filtrate was concentrated. The residue was purified by silica gel chromatography (eluate n-hexane: ethyl acetate=2:1 v/v) to obtain 5.84 g (97%) of the title compound as colorless powder.

Workup

  1. customwas performed at room temperature
  2. customAfter completion of the reaction, catalyst
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography (eluate n-hexane: ethyl acetate=2:1 v/v)

Sources & evidence

ORD record
ord-5061c0be22b4472e954f66723d78019f
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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