Sodium Hydroxide → 2-(Hydroxymethyl)-4-(trifluoromethyl)pyridine

HRID 2103406Notes

Reaction equation

HRID 2103406 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]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14761451[4-(Trifluoromethyl)pyridin-2-yl]methyl acetate

Product 1

HCID 147614592-(Hydroxymethyl)-4-(trifluoromethyl)pyridineYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

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

  1. extractionextracted with EtOAc twice
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0c404cfbe6894741a43fa89890001780
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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