Sodium hydride → HCID 86663364, compound

Participants

Reaction Steps

To a solution of trimethylsulfoxonium iodide (CAS#1774-47-6, 11.83 g, 53.8 mmol) in methyl sulfoxide (80 mL), was added slowly sodium hydride (60% dispersion in oil, 1.989 g, 49.7 mmol). The reaction was permitted to stir for 15 min at room temperature. A solution of 5-bromo-pyridine-3-carbaldehyde (CAS#135124-70-8, 5.0 g, 26.9 mmol) in dimethylsulfoxide (20 mL) was added slowly to the reaction mixture. The reaction permitted to stir for 10 minutes after the addition was complete. The reaction was cooled to 0° C., quenched with brine, and diluted with diethyl ether. The layers were separated and the aqueous layer was extracted two additional times with diethyl ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford 3-bromo-5-oxiranyl-pyridine; MS: (ES+) m/z 200.0 (M+H)+.

Provenance & Evidence