Ethanol → HCID 178471112, compound

HRID 349946Notes

Reaction equation

HRID 349946 reaction equation
C([O:8][C:9]1[CH:43]=[CH:42][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]([O:26]CC3C=CC(OCC4C=CC=CC=4)=CC=3)=[N:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)C>[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]([OH:26])=[N:15]2)=[CH:42][CH:43]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 69421593HCID 69421593, compound

Product 1

HCID 178471112HCID 178471112, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]propenoate (6.61 g), 5% palladium-carbon (13.00 g), ethanol (150 ml), and tetrahydrofuran (150 ml) was stirred for one hour at room temperature under a hydrogen atmosphere. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The crystals obtained were collected by filtration to yield ethyl 3-[1-(4-hydroxybenzyl)-3-hydroxy-1H-pyrazol-4-yl]propionate (2.98 g, yield: 89%). This was recrystallized from ethyl acetate-hexane. Melting point: 143–144° C.

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe crystals obtained
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3015501a6d1c4f75a08b73ecb602a21b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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