Ethanol → HCID 178471163, compound

HRID 349942Notes

Reaction equation

HRID 349942 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:20][CH2:21][CH3:22])=[N:9]1)C1C=CC=CC=1.C(O)C>[C].[Pd].C(O)=O>[CH2:21]([O:20][C:10]1[C:11]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][NH:8][N:9]=1)[CH3:22]

Participants

5

Reactant 2

HCID 702EthanolHCID 23024912ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate

Product 1

HCID 178471163HCID 178471163, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate (21.20 g), 5% palladium-carbon (40.00 g), ethanol (200 ml), and formic acid (100 ml) was refluxed for one hour. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was dissolved in ethyl acetate, which was washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(3-ethoxy-1H-pyrazol-4-yl)propionate (10.70 g, yield: 72%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturewas refluxed for one hour
  2. customAfter the palladium-carbon was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwhich was washed with saturated aqueous sodium bicarbonate
  6. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a04574051114ad59289ac9bdfa1a414
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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