Tetrahydrofuran → HCID 70141318, compound

HRID 349932Notes

Reaction equation

HRID 349932 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6]1[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:8][N:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[CH:10]=1)[CH3:2].O1CCCC1>[C].[Pd].C(O)C>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][N:9]2[CH:10]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33])[C:7]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:8]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86760427HCID 86760427, compound

Product 1

HCID 70141318HCID 70141318, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl(1-[2-(4-benzyloxyphenyl)ethyl]-3-phenyl-1H-pyrazol-4-yl)acetate (800 mg), 5% palladium-carbon (1.50 g), tetrahydrofuran (20 ml), and ethanol (30 ml) was stirred for 3 hours at room temperature under a hydrogen atmosphere. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and ethyl [1-[2-(4-hydroxyphenyl)ethyl]-3-phenyl-1H-pyrazol-4-yl]acetate (400 mg, yield: 63%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d679461a91fe409087ad89727a35e122
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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