Ethanol → HCID 178471111, compound

HRID 349940Notes

Reaction equation

HRID 349940 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:20]CC2C=CC=CC=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>[C].[Pd].O1CCCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([OH:20])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 69421683ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate

Product 1

HCID 178471111HCID 178471111, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate (14.30 g), 5% palladium-carbon (28.00 g), ethanol (150 ml), and tetrahydrofuran (150 ml) was stirred at room temperature for 3 hours 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-benzyl-3-hydroxy-1H-pyrazol-4-yl)propionate (9.01 g, yield: 83%). This was recrystallized from ethyl acetate-hexane. Melting point: 75–76° 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-0befb1316bdb49fe89d0a1c93051a29e
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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