反应详情

温度

-78 °C

To a solution of 1-bromo-4-chloro-5-(4-ethylbenzyl)-2-(2-(trifluoromethoxy)-ethoxy)benzene (BP) (60 mg, 0.14 mmol) and (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)-tetrahydropyran-2-one (0.19 g, 0.41 mmol) in anhydrous THF (2 mL), was added n-BuLi (2.5 M, 0.11 mL) in a dropwise fashion at −78° C. over 15 min. The resulting solution was stirred at −78° C. for 1 h. Methanesulfonic acid (20 μL in 0.5 mL MeOH) was added and the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was partitioned between EtOAc and saturated NaHCO3. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative TLC eluting with 5% MeOH in CH2Cl, to collect the crude product. To a solution of the crude product (10 mg, 0.018 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. was added Et3SiH (6.3 mg, 0.05 mmol) and BF3.Et2O (3.7 mg, 0.05 mmol). After stirring the resulting mixture for 1 h at 0° C., it was partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and evaporated under vacuum. The residue was purified by preparative HPLC to give compound BQ. 1H-NMR (CDCl3, 300 MHz) δ 7.21 (s, 1H), 7.07 (m, 4H), 6.89 (s, 1H), 4.29 (d, J=3.9 Hz, 1H), 4.17 (m, 2H), 4.01 (m, 2H), 3.81 (m, 2H), 3.76 (m, 1H), 3.74-3.49 (m, 6H), 2.61 (m, 3H), 1.20 (m, 3H).

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3
4. dry with materialThe organic layer was dried with anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by preparative TLC
8. washeluting with 5% MeOH in CH2Cl
9. customto collect the crude product
10. stirringAfter stirring the resulting mixture for 1 h at 0° C.
11. customit was partitioned between water and EtOAc
12. dry with materialThe organic layer was dried over Na2SO4
13. customevaporated under vacuum
14. customThe residue was purified by preparative HPLC
15. customto give compound BQ