Lithium hydroxide, monohydrate → 1-cyclopropyl-1H-pyrazole-3-carboxylic acid

HRID 1409388Notes

Reaction equation

HRID 1409388 reaction equation
[CH:1]1([N:4]2[CH:8]=[CH:7][C:6]([C:9]([O:11]C)=[O:10])=[N:5]2)[CH2:3][CH2:2]1.O[Li].O>C1COCC1.O>[CH:1]1([N:4]2[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[N:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86714649HCID 86714649, compound

Product 1

HCID 670305061-cyclopropyl-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-cyclopropyl-1H-pyrazole-3-carboxylate (2.5 g, 15 mmol) was dissolved in THF (40 ml) and H2O (10 ml). LiOH.H2O (1.50 g, 22.5 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was concentrated and acidified to pH 2 using 1 N HCl. The mixture was extracted with EtOAc and the organic layer was concentrated. Yield 1.6 g. 1H-NMR (400 MHz; DMSO-d6): δ 0.96-1.02 (m, 2H), 1.04-1.09 (m, 2H), 3.79-3.84 (m, 1H), 6.66 (d, 1H), 7.88 (d, 1H), 12.6 (bs, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-87b6905f021b44f7a8db457a0f750b70
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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