Methanol → (2-Trifluoromethylpyrazolo[1,5-a]pyridin-3-yl)methanol
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[C:11]([C:12](OCC)=[O:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[OH-].[Na+]>O1CCCC1>[F:18][C:2]([F:1])([F:17])[C:3]1[C:11]([CH2:12][OH:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of 2.8 g (11 mmol) of ethyl 2-trifluoromethylpyrazolo[1,5-α]pyridine-3-carboxylate in 50 ml of tetrahydrofuran is added dropwise to a suspension of 0.5 g (12 mmol) of lithium aluminum hydride in 45 ml of tetrahydrofuran. The reaction medium is then stirred at 70° C. for 3 h. After dropwise addition of 2.5 ml of methanol and then of 1.8 ml of an aqueous solution of sodium hydroxide having a concentration of 2N, the reaction medium is stirred for 20 min at ambient temperature and then filtered. The filtrate is dried over magnesium sulfate, filtered and concentrated under vacuum. 2.3 g (100%) of (2-trifluoromethylpyrazolo[1,5-α]pyridin-3-yl)methanol are obtained in the form of a solid.
Workup
- filtrationfiltered
- dry with materialThe filtrate is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-49d28d1410bb4a46b67147385a039a39
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365529B2
Reaction notes
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