Methanol → HCID 14459971, compound

Participants

Reaction Steps

To a solution of methyl 5-(dibromomethyl)pyridine-2-carboxylate (927 mg, 3.00 mmol) in methanol (10 ml) and trimethyl orthoformate (2 ml) was added a solution AgNO3 (1.12 g, 6.6 mmol) in methanol (20 ml) over 15 minutes. After refluxing the reaction for 1 hour, it was cooled and poured into a solution of NaHCO3 (0.84 g, 10 mmol) in water (50 ml) containing a small amount of NaCl. The thick slurry was filtered through a 25-50 micron frit, and the filtrate concentrated to 10 ml and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried (MgSO4), filtered and concentrated to give title product (550 mg, 96%).

Provenance & Evidence