HCID 53707664, compound → HCID 23298348, compound

HRID 427281Notes

Reaction equation

HRID 427281 reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:9][CH:8]=1)[CH3:2].[H][H]>O1CCOCC1.[Pd]>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:11][CH:12]=1)[CH3:23]

Participants

5

Reactant 2

HCID 53707664HCID 53707664, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23298348HCID 23298348, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-[4-[(2,2-diethoxy)ethoxy]phenyl methylene]thiazolidin-2,4-dione (8.0 g, 23.7 mmol) obtained in example 1, in 1,4-dioxane (100 mL) was reduced with hydrogen in the presence of 10% palladium on charcoal (16.0 g) at 60 psi for 60 h. The mixture was filtered through a bed of celite. The filtrate was evaporated to dryness under reduced pressure; purified by column chromatography using EtOAc:pet. ether (1:1) as an eluent to afford the title compound (8.04 g, 67%) as a colourless liquid.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-247f4ca3381a41479752c15ff69fd7de
Source dataset
uspto-grants-2001_11
Patent number
US06313113B1

Reaction notes

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