HCID 68985641, compound → HCID 68984719, compound

HRID 475589Notes

Reaction equation

HRID 475589 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20](/[CH:22]=[CH:23]/[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH2:33][CH2:34][CH3:35])=[O:25])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH2:33][CH2:34][CH3:35])=[O:25])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 68985641HCID 68985641, compound

Product 1

HCID 68984719HCID 68984719, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 1.82 g quantity of (E)-3-[2-(3-benzyloxy-4-methoxyphenyl)oxazol-4-yl]-1-(2-propoxyphenyl)-2-propen-1-one obtained in Example 193 was dissolved in 50 ml of methanol. A 200 mg quantity of 5% palladium-carbon powder was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours. The catalyst was then removed by filtration. The filtrate was diluted with 100 ml of methanol, and 500 mg of 10% palladium-carbon powder was added thereto. The mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. The catalyst was removed by filtration, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the residue for crystallization to give 0.78 g of colorless powdery 3-[2-(3-hydroxy-4-methoxyphenyl)oxazol-4-yl]-1-(2-propoxyphenyl)propan-1-one.

Workup

  1. customThe catalyst was then removed by filtration
  2. additionThe filtrate was diluted with 100 ml of methanol, and 500 mg of 10% palladium-carbon powder
  3. additionwas added
  4. stirringThe mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours
  5. customThe catalyst was removed by filtration
  6. customthe solvent was removed under reduced pressure
  7. additionDiisopropyl ether was added to the residue for crystallization

Sources & evidence

ORD record
ord-2033458ce6984dd9881133a3bc060aec
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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