Sulfoxonium, trimethyl-, iodide (1:1) → HCID 66788167, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of trimethylsulfoxonium iodide (CAS#1774-47-6, 6.38 g, 29.0 mmol) in tert-butanol (20 mL), was added potassium tert-butoxide (3.25 g, 29.0 mmol). The reaction was heated to 50° C. and permitted to stir for 15 min. A solution of 3-bromo-5-oxiranyl-pyridine (2.9 g, 14.50 mmol) in tert-butanol (20 mL) was then added slowly to the reaction. The reaction was permitted to stir at 50° C. for 16 hr. The reaction mixture was cooled to 0° C., quenched with brine, and diluted with diethyl ether. The layers were separated and the aqueous layer was extracted with diethyl ether two additional times. 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-oxetan-2-yl-pyridine; MS: (ES+) m/z 214.3 (M+H)+.

Provenance & Evidence