methyl 3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate → methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate

HRID 349904Notes

Reaction equation

HRID 349904 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:15]2)=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 23024803methyl 3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate

Product 1

HCID 23024960methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionateYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (500 mg), 5% palladium-carbon (1.00 g), and tetrahydrofuran (10 ml) was stirred for 18 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 methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (325 mg, yield: 80%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 87–88° C.

Workup

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

Sources & evidence

ORD record
ord-99f90e1a84af43e7b5d00838ad25c190
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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