Benzyl 2-(1-methyl-1H-pyrazol-3-yl)acrylate → 2-(1-methyl-1H-pyrazol-3-yl)propanoic acid

HRID 887138Notes

Reaction equation

HRID 887138 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7](=[CH2:18])[C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[N:3]1>[Pd].CO>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:18])[C:8]([OH:10])=[O:9])=[N:3]1

Participants

4

Reactant 1

HCID 66839543Benzyl 2-(1-methyl-1H-pyrazol-3-yl)acrylate

Product 1

HCID 579074952-(1-methyl-1H-pyrazol-3-yl)propanoic acidYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.10 mg (0.093 mmol) of 10% palladium on carbon was added a solution of (0.23 g, 0.93 mmol) of benzyl 2-(1-methyl-1H-pyrazol-3-yl)acrylate prepared in step C above in 6 mL of methanol. The resulting suspension was stirred under an atmosphere of hydrogen (1 atmosphere) overnight. The residue was filtered through a pad of Celite® and the pad was washed with cold methanol. The combined filtrates were evaporated under reduced pressure to yield the title compound as an off-white gum (0.11 g, 76%). LC-MS: m/z (ES) 155 (MH)+.

Workup

  1. filtrationThe residue was filtered through a pad of Celite®
  2. washthe pad was washed with cold methanol
  3. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-909716ea17ed40cda7f3dff13c6f5138
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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