Lithium hydroxide, monohydrate → 1-cyclopropyl-1H-pyrazole-3-carboxylic acid
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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- concentrationThe reaction mixture was concentrated
- extractionThe mixture was extracted with EtOAc
- 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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