Sodium Hydroxide → 5-(3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:23])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4].[OH-].[Na+]>O1CCOCC1.O>[CH2:19]([C:13]1[C:12]([CH2:11][O:10][C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:23])[N:7]=2)=[C:16]([CH2:17][OH:18])[O:15][N:14]=1)[CH2:20][CH2:21][CH3:22]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 5-(3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (260 mg, 0.81 mmol) in dioxane (15 mL) was added aqueous sodium hydroxide (2 M, 7.0 mL, 7.0 mmol). After heating at 90° C. for 1.5 h the solution was cooled to room temperature, diluted with water, extracted with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated to afford the title compound (250 mg, 100%) as a white solid. MS: m/e=308.5 [M−H]−.
Workup
- temperaturewas cooled to room temperature
- extractionextracted with ethyl acetate
- washthe combined organic phases were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bca374ef06b54ce9b3ce1d5ffb88610d
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163728B2
Reaction notes
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