Sodium Hydroxide → 2-(Hydroxymethyl)-4-(trifluoromethyl)pyridine
Reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>CO.O>[F:14][C:12]([F:13])([F:15])[C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[CH:11]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of [4-(trifluoromethyl)pyridin-2-yl]methyl acetate (1.0 g, 3.2 mmol) in methanol (10 mL) was added a 1.0 M solution of sodium hydroxide in water (10 mL). After being stirred at room temperature overnight, the solution was diluted with 20 mL of water and extracted with EtOAc twice. The combined organic layers were dried (MgSO4) and concentrated under vacuum. Chromatography on silica gel eluting with hexanes/EtOAc (1:1) afforded the title compound (0.34 g) as a clear oil. MS (M+H) 178.1.
Workup
- extractionextracted with EtOAc twice
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-0c404cfbe6894741a43fa89890001780
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576089B2
Reaction notes
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