Formic Acid → HCID 178440435, compound

HRID 349918Notes

Reaction equation

HRID 349918 reaction equation
C([N:8]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=[N:9]1)C1C=CC=CC=1.C(O)=O>[C].[Pd].C(O)C>[CH2:13]([C:12]1[C:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][NH:9][N:8]=1)[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 69421629HCID 69421629, compound

Product 1

HCID 178440435HCID 178440435, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl(E)-3-(1-benzyl-5-propyl-1H-pyrazol-4-yl)propenoate (6.00 g), 5% palladium-carbon (12.0 g), formic acid (50 ml), and ethanol (100 ml) was refluxed for 16 hours. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(3-propyl-1H-pyrazol-4-yl)propionate (3.45 g, yield: 82%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customAfter the palladium-carbon was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f4502d0b669d4417b448c7724756656e
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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