反应详情

温度

0 °C

A solution of alcohol 56 (163 mg, 0.5 mmol) in anhydrous DMF (7 mL) was cooled to 0° C. NEt3 (0.14 mL, 1 mmol) and MsCl (47 λL, 0.6 mmol) were added successively and the reaction mixture was stirred at 0° C. for 1 h. K2CO3 (138 mg, 1 mmol) and 4-methylthiophenol (68 mg, 0.55 mmol) were added and the reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was then cooled to 20° C. and partitioned between EtOAc (200 mL) and H2O (50 mL). The organic fraction was washed with H2O (2×50 mL), washed with brine (50 mL), and dried. The solvent was evaporated to give the crude sulfide (158 mg, 0.37 mmol) which was used without further purification. A solution of Oxone® (172 mg, 0.28 mmol) in H2O (3 mL) was added at 0° C. to a stirred solution of crude sulfide (88 mg, 0.2 mmol) in MeOH (3 mL), and the reaction mixture was stirred for 1 h at 20° C. H2O was added (50 mL), the mixture was extracted with DCM (3×50 mL) and the organic phase was washed with brine (50 mL), dried, and the solvent was evaporated. Remaining sulfide (70 mg, 0.16 mmol) was treated as described and the combined crude products were purified by column chromatography, eluting with 5% MeOH/EtOAc, to give sulfone 9 (65 mg, 28%) as a white powder: spectroscopically identical to the sample prepared above.

1. stirringthe reaction mixture was stirred at 60° C. for 1 h
2. temperatureThe reaction mixture was then cooled to 20° C.
3. custompartitioned between EtOAc (200 mL) and H2O (50 mL)
4. washThe organic fraction was washed with H2O (2×50 mL)
5. washwashed with brine (50 mL)
6. customdried
7. customThe solvent was evaporated
8. customto give the crude sulfide (158 mg, 0.37 mmol) which
9. customwas used without further purification
10. stirringthe reaction mixture was stirred for 1 h at 20° C
11. extractionthe mixture was extracted with DCM (3×50 mL)
12. washthe organic phase was washed with brine (50 mL)
13. customdried
14. customthe solvent was evaporated
15. customthe combined crude products were purified by column chromatography
16. washeluting with 5% MeOH/EtOAc