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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- customwas subjected to catalytic hydrogenation at room temperature under atmospheric pressure
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe concentrate was purified by means of a silica gel column chromatography
- washFrom the fractions eluted with chloroform-methanol (100:3)
Sources & evidence
- ORD record
- ord-62785fad55c348eda698dd1cf279408e
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552058B1
Linked notes
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