Sodium borohydride → {6-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}methanol

HRID 890452Notes

Reaction equation

HRID 890452 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>CCO>[F:19][C:2]([F:1])([F:18])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219356276-[4-(Trifluoromethoxy)phenyl]-3-pyridinecarboxaldehyde

Product 1

HCID 21935933{6-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(4-Trifluoromethoxy-phenyl)-pyridine-3-carbaldehyde (2.0 g, 7.48 mmol) was dissolved in EtOH (37 ml) and treated at 0° C. with NaBH4 (0.28 g, 7.48 mmol). After 10 min the cooling bath was removed and stirring was continued at ambient temperature. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents afforded 2.08 g (7.7 mmol, quant.) of the title compound as off-white solid of mp. 57–58° C.

Workup

  1. customAfter 10 min the cooling bath was removed
  2. customwas continued at ambient temperature
  3. additionPouring
  4. extractionice, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7bc585eb9922453aa15e6d53fae9c526
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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