ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate → ethyl 3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propionate

HRID 1295262Notes

Reaction equation

HRID 1295262 reaction equation
[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[C].[Pd].O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][N:11]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86591670ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate

Product 1

HCID 22930669ethyl 3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propionateYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate (2.70 g), 5% palladium-carbon (3.00 g) and tetrahydrofuran (100 ml) was stirred under a hydrogen atmosphere at room temperature for 3 hrs. Palladium-carbon was filtered off and the filtrate was concentrated. The obtained crystals were collected by filtration to give ethyl 3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propionate (1.78 g, yield 89%), which was then recrystallized from ethyl acetate-hexane. melting point: 123–124° C.

Workup

  1. filtrationPalladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-6d5d5152a62b4a5aae7e175a3dd765a4
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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