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

HRID 349996Notes

Reaction equation

HRID 349996 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][N:14]2[CH:18]=[C:17](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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][CH2:24][CH3:25])=[O:22])[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:15]2)=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 69427016ethyl(E)-3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propenoate

Product 1

HCID 23024792ethyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionateYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propenoate (12.13 g), 5% palladium-carbon (10.22 g) and tetrahydrofuran (100 ml) was stirred for 5 hours under a hydrogen atmosphere. After the palladium-carbon was removed by filtration, the filtrate was concentrated to obtain ethyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (9.52 g, yield 98%) as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-a86918e8de2c44629b466c737c88bbae
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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