Sodium Hydroxide → (2-Trifluoromethylpyrazolo[1,5-a]pyridin-3-yl)methanol

HRID 517525Notes

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-].[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]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 2.8 g (10.8 mmol) of ethyl 2-trifluoromethylpyrazolo[1,5-a]pyridine-3-carboxylate in 50 ml of tetrahydrofuran is added dropwise to a mixture of 0.5 g (11.9 mmol) of lithium aluminium hydride in suspension in 45 ml of tetrahydrofuran at −70° C. After stirring for 3 h at −70° C., the mixture is brought to ambient temperature, then 1.8 ml of a 2N aqueous sodium hydroxide solution is added. The mixture is filtered, dried over magnesium sulphate, filtered and concentrated. 2.3 g (100%) of (2-trifluoromethylpyrazolo[1,5-a]pyridin-3-yl)methanol are obtained in the form of a yellow solid.

Workup

customis brought to ambient temperature
filtrationThe mixture is filtered
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f1477196bf194b5dba857494b31a2c8f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115102B2

Reaction notes

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