ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate → ethyl 3-(3-hydroxy-1-phenyl-1H-pyrazol-5-yl)propanoate

HRID 1295278Notes

Reaction equation

HRID 1295278 reaction equation
C([O:8][C:9]1[CH:13]=[C:12](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)C1C=CC=CC=1>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:11]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:10]=1

Participants

4

Reactant 1

HCID 86591672ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate

Product 1

HCID 178471103ethyl 3-(3-hydroxy-1-phenyl-1H-pyrazol-5-yl)propanoateYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate (7.33 g), 5% palladium-carbon (7.11 g) and tetrahydrofuran (50 ml) was stirred overnight under a hydrogen atmosphere at room temperature. Palladium-carbon was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(3-hydroxy-1-phenyl-1H-pyrazol-5-yl)propionate (4.85 g, yield 89%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from acetone-hexane. melting point: 150–151° C.

Workup

  1. filtrationPalladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ddc4f24228e845c39104a2e6f6610c23
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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