反应详情

温度

0 °C

To a THF (0.1 M) solution of N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide (1 eq.) from the previous step and freshly distilled TMEDA (1 eq.) was added at −78° C. t-butyl lithium (1.7 M in pentanes, 1 eq.) dropwise over 10 min. The resulting reaction mixture was then slowly warmed to 0° C. over 1 h and stirred at 0° C. for 1 h. With the now orange reaction solution re-cooled to −78° C., 1,2-dibromotetrafluoroethane was added neat, dropwise over 10 min. The cooling bath was removed and the reaction mixture was stirred at RT for 18 h. The reaction was then quenched with 1 N aq. NaOH and extracted with EtOAc. The combined organic extracts were washed further with 10% aq. HCl, water and brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a pale yellow oil.

1. customThe resulting reaction mixture
2. temperatureWith the now orange reaction solution re-cooled to −78° C.
3. customThe cooling bath was removed
4. stirringthe reaction mixture was stirred at RT for 18 h
5. customThe reaction was then quenched with 1 N aq. NaOH
6. extractionextracted with EtOAc
7. washThe combined organic extracts were washed further with 10% aq. HCl, water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationthe filtrate concentrated in vacuo
11. customPurification of the crude product
12. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)