Benzyl Alcohol → 2-benzyloxy-5-nitro-pyridine

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (682 mg, 6.3 mmol), 18 crown ether (2.5 g, 9.4 mmol) and KOH (637 mg, 11.3 mmol) were added to a solution of 2-chloro-5-nitro-pyridine (1 g, 6.3 mmol) in toluene (15 mL) and the reaction mixture was maintained at 80° C. for 2 hours, then diluted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and evaporated. The residue was purified by column chromatography using neutral alumina (2% ethyl acetate in hexane) to afford 410 mg (28%) of 2-benzyloxy-5-nitro-pyridine. LCMS: 231.07 (M+1)+, 98.4%

Provenance & Evidence