5-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione → 5-[3-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]propyl]-2,4-oxazolidinedione

HRID 1857513Notes

Reaction equation

HRID 1857513 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:32]=[CH:31][C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[O:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1>[C].[Pd].O1CCOCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH2:22][CH2:23][CH:24]2[O:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 570370095-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione

Product 1

HCID 158724295-[3-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]propyl]-2,4-oxazolidinedioneYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione (0.29 g), palladium-carbon (10%, 0.1 g) and dioxane (50 ml) was subjected to catalytic hydrogenation at room temperature under atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:3) was obtained 5-[3-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]propyl]-2,4-oxazolidinedione (0.28 g, 96%). This product was recrystallized from dichloromethane-methanol to give colorless prisms, m.p.149-150° C.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature under atmospheric pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe concentrate was purified by means of a silica gel column chromatography
  5. washFrom the fractions eluted with chloroform-methanol (100:3)

Sources & evidence

ORD record
ord-a552c86f7a9240e1ae3868e06a4785e1
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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