反应详情

温度

-65 °C

To a −65° C. solution of (S)-3-(2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethoxy)tetrahydrofuran (200 mg, 0.49 mmol) in anhydrous toluene/tetrahydrofuran (6 mL, v/v=2:1) was added dropwise n-butyllithum (2.5 M in hexane, 0.3 mL), and the pale yellow mixture was stirred for 30 min at −65° C. The mixture was transferred to a −65° C. solution of (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one (280 mg, 0.73 mmol) in toluene (4 mL). The mixture was stirred at −65° C. for 2 h until starting material was consumed. The reaction was quenched with methanesulfonic acid (0.04 mL, 1.7 mmol) in methanol (6 mL), and the mixture was allowed to warm to 20° C. and stirred overnight. The reaction was quenched with saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate, then with water and then with brine prior to drying over anhydrous sodium sulfate. Removal of volatiles afforded 200 mg of crude solid product, which was used in the next step without further purification.

1. customwas transferred to a −65° C.
2. stirringThe mixture was stirred at −65° C. for 2 h
3. customwas consumed
4. temperatureto warm to 20° C.
5. stirringstirred overnight
6. customThe reaction was quenched with saturated sodium bicarbonate
7. customThe organic phase was separated
8. extractionthe aqueous phase was extracted with ethyl acetate
9. washwashed with saturated sodium bicarbonate
10. dry with materialwith water and then with brine prior to drying over anhydrous sodium sulfate
11. customRemoval of volatiles