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

HRID 1357201Notes

Reaction equation

HRID 1357201 reaction equation
[CH3:1][C:2]1[C:3](=[O:27])[O:4][C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]=[C:20]4[C:24](=[O:25])[NH:23][C:22](=[O:26])[S:21]4)=[CH:15][C:13]=3[CH:14]=2)=[C:6]([CH3:9])[C:7]=1[OH:8].CCO.[H][H]>[Pd].O1CCOCC1>[CH3:1][C:2]1[C:3](=[O:27])[O:4][C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]4[C:24](=[O:25])[NH:23][C:22](=[O:26])[S:21]4)=[CH:15][C:13]=3[CH:14]=2)=[C:6]([CH3:9])[C:7]=1[OH:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 547366073,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinylidene)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 865897203,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinyl)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinylidene) methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one (350 mg) in a mixed solvent of EtOH (10 ml) and 1,4-dioxane (10 ml) there was added 10% Pd/C (70 mg), and the mixture was stirred for one day in a hydrogen gas atmosphere. The reaction solution was filtered, the mother liquor was concentrated under reduced pressure, and then 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-thiazolidinyl)methyl)benzofuran-2-yl)-4-hydroxy-2H-pyran-2-one.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=5/1)

Sources & evidence

ORD record
ord-1bc31d8de74e4175af82c1051e03ceb7
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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