反应详情

温度

-40 °C

In anhydrous equipment under a nitrogen atmosphere was stirred a mixture of 2-(4-tolylsulfanyl)-phenyl bromide (600 g, 2.15 mol) in heptanes (4.5 L) at room temperature (25° C.). n-Bu-lithium (10 M, 236 mL) solution in heptane was then added by canulation. After stirring at room temperature for 30 minutes the reaction mixture was cooled to −50° C. before a solution of carbetoxypiperidone in THF (1.5 L) was added dropwise while maintaining the temperature under −40° C. Once the addition was completed, reaction was allowed to warm to 0° C. before dilute HCl (1 L) was added maintaining the temperature below 10° C. Once addition was complete reaction was stirred for a further 15 minutes before phases where allowed to separate. Phases were separated, the water layer was extracted with ethyl acetate (1 L) and the organic layers combined. The combined organic layer was washed with NaCl solution (15%) (1 L), dried over magnesium sulphate, evaporated to dryness and slurried in diethyl ether (250 mL) for 30 minutes, filtered and dried at 40° C. in a vacuum oven. Yield 55-60%.

1. stirringAfter stirring at room temperature for 30 minutes the reaction mixture
2. additionwas added dropwise
3. additionOnce the addition
4. customreaction
5. additionwas added
6. temperaturemaintaining the temperature below 10° C
7. additionOnce addition
8. customreaction
9. stirringwas stirred for a further 15 minutes before phases where
10. customto separate
11. customPhases were separated
12. extractionthe water layer was extracted with ethyl acetate (1 L)
13. washThe combined organic layer was washed with NaCl solution (15%) (1 L)
14. dry with materialdried over magnesium sulphate
15. customevaporated to dryness
16. filtrationfiltered
17. customdried at 40° C. in a vacuum oven