反应详情

温度

-75 °C

A 1 L three-neck flask was charged with N-tert-butyl-5-chlorothiophene-2-carboxamide (10.0 g, 45.9 mmol) and thoroughly flushed with nitrogen gas. The flask was charged with THF (400 ml) by cannulation, then cooled to −75° C. Tert-butyllithium, 1.7 m solution in pentane (68.4 ml, 116 mmol) was added by syringe pump over 45 min, keeping the temperature less than −70° C. After stirring at −75° C. for 90 min, the reaction was gradually warmed to −60° C. and stirred for 1 hr. The mixture was again cooled to −75° C. and DMF (14.2 ml, 184 mmol) was added dropwise, ensuring the temperature remained below −70° C. The mixture was stirred at −75° C. for 1 hr. The reaction was quenched with 200 ml sat. aq. NH4Cl, then allowed to warm to RT. Water was added to the solution to dissolve solids and the mixture was extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated to give the title compound as a tan solid (11.6 g.). MS (ESI, pos. ion) m/z: 246 (M+1).

1. customthoroughly flushed with nitrogen gas
2. additionThe flask was charged with THF (400 ml) by cannulation
3. customthe temperature less than −70° C
4. temperaturethe reaction was gradually warmed to −60° C.
5. stirringstirred for 1 hr
6. temperatureThe mixture was again cooled to −75° C.
7. customremained below −70° C
8. stirringThe mixture was stirred at −75° C. for 1 hr
9. customThe reaction was quenched with 200 ml sat. aq. NH4Cl
10. temperatureto warm to RT
11. additionWater was added to the solution
12. dissolutionto dissolve solids
13. extractionthe mixture was extracted with EtOAc (3×)
14. dry with materialThe combined organics were dried over Na2SO4
15. filtrationfiltered
16. concentrationconcentrated