Benzyl Alcohol → 6-(Benzyloxy)pyridine-3-carbonitrile

HRID 1177902Notes

Reaction equation

HRID 1177902 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH2:10]([O:17][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 247001066-(Benzyloxy)pyridine-3-carbonitrileYield 40.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6-chloronicotinonitrile (1 g, 7.2 mmol) and benzyl alcohol (780 mg, 7.2 mmol) in toluene (15 mL) was added KOH (729 mg, 12.99 mmol) and 18 crown ether (2.86 g, 10.8 mmol). The resulting mixture was stirred at 70° C. for 7 hrs. The mixture was diluted with cold water and the product was extracted with EtOAc. The organic layer was washed with saturated brine solution and dried over Na2SO4. The organic layer was then concentrated under reduced pressure. The obtained residue was purified by column chromatography (using neutral alumina and 5% MeOH: CHCl3 as eluent) to afford 610 mg (40.1% yield) of 6-benzyloxy-nicotinonitrile. LCMS Purity: 77.69%.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layer was then concentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (using neutral alumina and 5% MeOH: CHCl3 as eluent)

Sources & evidence

ORD record
ord-19efeb69868d4291a959ed5671a38cef
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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