HCID 21909294, compound → HCID 21909297, compound

HRID 1247746Notes

Reaction equation

HRID 1247746 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-a8b8591ec94c4f4f970fb0fcf0242c40
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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