HCID 21909294, compound → HCID 21909297, compound

HRID 1826652Notes

Reaction equation

HRID 1826652 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:24][C:25]([NH2:27])=[O:26])[CH:12]=[CH:13][C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([CH2:24][C:25]([NH2:27])=[O:26])=[CH:10][C:9]=2[OH:8])=[CH:17][CH:18]=1)[CH3:23]

Participants

4

Reactant 1

HCID 21909294HCID 21909294, compound

Product 1

HCID 21909297HCID 21909297, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[3-benzyloxy-4-(4-ethylbenzyl)phenyl]acetamide (0.38 g) in methanol (5 mL) was added 10% palladium-carbon powder (0.075 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hours. An insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=30/1–20/1) to give 2-[4-(4-ethylbenzyl)-3-hydroxyphenyl]acetamide (0.16 g).

Workup

  1. customAn insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=30/1–20/1)

Sources & evidence

ORD record
ord-8adeeda1aba146ebaba58fd71a164d49
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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