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]=1To 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%.
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