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

Temperature

50 °C

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)+.

1. stirringto stir at 50° C. for 16 hr
2. temperatureThe reaction mixture was cooled to 0° C.
3. customquenched with brine
4. additiondiluted with diethyl ether
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with diethyl ether two additional times
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%)

ORD record

ord-5931e1fdd7c84fb9ad3af53fe4b33f74

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778972B2