Ethanol → 2-(1-Cyclopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)acetic acid
Reaction equation
[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7](CC#N)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.[OH-:16].[Na+].[CH3:18][CH2:19][OH:20]>>[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([CH2:18][C:19]([OH:16])=[O:20])[CH:6]=[N:5]2)[CH2:3][CH2:2]1Participants
4
Conditions
- Temperature
- 60 °C
Procedure
To a solution of (1-Cyclopropyl-5-trifluoromethyl-1H-pyrazol-4-yl)-acetonitrile (Preparation 139, 700 mg, 3.25 mmol) in EtOH (15 mL) was added aqueous 1N NaOH (15 mL). The resulting solution was heated at 60° C. for 16 hours. The mixture was concentrated and the residue was dissolved in water (10 mL) and washed with EtOAc. The pH of aqueous layer was adjusted to 5 using 1N HCl and extracted with 10% IPA in DCM (4×30 mL). The organic layer was dried (Na2SO4) and evaporated in vacuo to afford the title compound as a solid in 85% yield, 650 mg.
Workup
- concentrationThe mixture was concentrated
- dissolutionthe residue was dissolved in water (10 mL)
- washwashed with EtOAc
- extractionextracted with 10% IPA in DCM (4×30 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-e81e96c2f7114dd18bf0f0e8f3606980
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846698B2
Reaction notes
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