Hydrochloric Acid → (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acid

HRID 30682

Reaction equation

HRID 30682 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11]CC)=[O:10])[CH:4]=[N:3]1.CO.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68356132(E)-Ethyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate

Product 1

HCID 1529858(2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate (2.5 g), methanol (20 ml) and tetrahydrofuran (20 ml) was added a 2N aqueous sodium hydroxide solution (13.9 ml) and the mixture was stirred at 60° C. for 3 hrs. 1N Hydrochloric acid was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to give (2E)-3-(1-methyl-1H-pyrazol-4-yl)acrylic acid (1.75 g, 83%) as an amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3995dd47bdf448cb9568a52cff09b20
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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