Water → 1-(Pyridin-3-yl)propan-1-ol

HRID 932179Notes

Reaction equation

HRID 932179 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:10])[CH2:8][CH3:9])[CH:2]=1.[BH4-].[Na+].O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:10])[CH2:8][CH3:9])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 740741-(3-Pyridyl)propan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 110839421-(Pyridin-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(pyridin-3-yl)propan-1-one (2.46 g, 18.20 mmol, purchased from Lancaster Synthesis Ltd.) in MeOH (15 mL) at rt under N2 atmosphere was added sodium borohydride powder (0.690 g, 18.20 mmol). After stirring at rt for 1.5 hr, to the reaction solution was added water (20 ml). The resulting mixture was stirred for 4 min, extracted with EtOAc (20 mL×3). The organic layers were combined, washed with water, sat. aq. NaCl solution and dried over MgSO4. Removal of the solvents provided the crude title compound as white solid. Mass Spectrum (ESI) m/z=138.0 (M+1).

Workup

  1. stirringThe resulting mixture was stirred for 4 min
  2. extractionextracted with EtOAc (20 mL×3)
  3. washwashed with water, sat. aq. NaCl solution
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvents

Sources & evidence

ORD record
ord-d305396eaa1e429a923df1fe06ae61bd
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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