Hydrochloric Acid → 3-(Trifluoromethyl)-1H-pyrazole-4-carboxylic acid
Reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:15])([F:14])[C:6]1[NH:10][N:9]=[CH:8][C:7]=1[C:11]([O-:13])=[O:12].CO.Cl>O.C1COCC1>[F:15][C:5]([F:4])([F:14])[C:6]1[NH:10][N:9]=[CH:8][C:7]=1[C:11]([OH:13])=[O:12]Participants
7
Procedure
A solution of lithium hydroxide hydrate (1.265 g, 30.2 mmol) in water was added to a solution of ethyl 1-(((+/−)cis)-2-allylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate as a racemate (0.996 g, 3.02 mmol) in THF and MeOH and the mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo. The resulting turbid solution was diluted with water to provide a clear solution. The pH was adjusted to 1 by adding 1 M HCl and the mixture was stirred vigorously for 30 min. The resulting precipitate was collected by vacuum filtration to provide 1-(((+/−)-cis)-2-allylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid as a racemate (D60) as a white solid.
Workup
- concentrationThe mixture was concentrated in vacuo
- additionThe resulting turbid solution was diluted with water
- customto provide a clear solution
- filtrationThe resulting precipitate was collected by vacuum filtration
Sources & evidence
- ORD record
- ord-aede431f66ea43ea97388af483bba69a
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365522B2
Reaction notes
Loading…