HCID 10551486, compound → 1,3-Diethyl 2-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]propanedioate

HRID 1532750Notes

Reaction equation

HRID 1532750 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:33]=[CH:32][C:19]([CH:20]=[C:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1>CO.O1CCCC1.[C].[Pd]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][CH:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:32][CH:33]=1

Participants

5

Reactant 1

HCID 10551486HCID 10551486, compound

Product 1

HCID 117978601,3-Diethyl 2-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]propanedioateYield 55%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidenemalonate (9.55 g, 21.3 mmol) obtained in Example 54 was dissolved in methanol (48 ml) and tetrahydrofuran (32 ml). 5% Palladium carbon (1 g) was added and the mixture was vigorously stirred at normal temperature under a hydrogen atmosphere (3.1 kgf/cm2). One and a half hours later, the catalyst was filtered off. The solvent was evaporated to give a crude solid. Recrystallization from ethyl acetate-hexane gave the title compound (5.23 g, yield 55%) as white crystals.

Workup

  1. filtrationOne and a half hours later, the catalyst was filtered off
  2. customThe solvent was evaporated
  3. customto give a crude solid
  4. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e33ee117cbab4e1c8eb07290d8b13038
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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