Pyridine → HCID 117665492, compound

Participants

Reaction Steps

A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with MeOTf (116 μL, 1.06 mmol) by micropipette. The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with 4-methoxy-2-pyridinecarboxaldehyde (Astatech C10253, 145 mg, 106 mmol) and was dissolved in PhMe (1 mL). The solution of pyridine was added via syringe onto the MeOTf at room temperature. The vial which contained the pyridine was rinsed with PhMe (0.5 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. After 20 h, hexanes (2 mL) were added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The solid or oil was then rinsed with several portions of hexanes followed by diethyl ether. Residual solvent was then removed in vacuo to provide the compound N-methyl-4-methoxy-2-pyridinecarboxaldehyde triflate (300 mg, 94%). This oil was used for oxime formation without further purification.

Provenance & Evidence