Sodium Hydroxide → (6-(3-(Trifluoromethyl)phenyl)pyridin-3-YL)methanol

HRID 33511Notes

Reaction equation

HRID 33511 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:24])([F:23])[C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1.[OH-].[Na+]>O1CCCC1>[F:23][C:8]([F:7])([F:24])[C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 247297396-(3-Trifluoromethylphenyl)pyridine-3-carboxaldehyde

Product 1

HCID 24729887(6-(3-(Trifluoromethyl)phenyl)pyridin-3-YL)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

261 mg (6.87 mmol) lithium aluminium hydride were given to 20 ml tetrahydrofuran (THF) and stirred at room temperature (r.t.) for 20 min. A solution of 1.15 g (4.58 mmol) 6-(3-Trifluoromethyl-phenyl)-pyridine-3-carbaldehyde in 20 ml THF was added drop by drop within 15 min., and the mixture stirred for 3 h. 1.5 ml ice water and 0.6 ml 2 M NaOH were added slowly at 0° C. and stirred continued for 30 min. A formed salt precipitate was isolated by filtration and washed with THF. The combined THF-solutions were evaporated, the residue extracted twice with ethyl acetate, the organic phase dried (sodium sulphate), evaporated, and the obtained material (0.98 g, 85%) used without further purification.

Workup

  1. stirringthe mixture stirred for 3 h
  2. stirringstirred
  3. waitcontinued for 30 min
  4. customA formed salt precipitate was isolated by filtration
  5. washwashed with THF
  6. customThe combined THF-solutions were evaporated
  7. extractionthe residue extracted twice with ethyl acetate
  8. dry with materialthe organic phase dried (sodium sulphate)
  9. customevaporated
  10. customthe obtained material (0.98 g, 85%) used without further purification

Sources & evidence

ORD record
ord-f5d4408f9aec4ef79a13acf54bfa5a6a
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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