反应详情

Added LHMDS (1603 μl, 1.603 mmol, 1M in THF) to 1-3 (422 mg, 1.679 mmol) in THF (1908 μl) at −78° C. Removed cooling bath and stirred at RT for 30 min. Cooled back to −78 C and slowly added the 35-2 (159 mg, 0.509 mmol) in THF (636 μl). The resulting reaction mixture was allowed to slowly warm to RT while remaining in bath. After 2 h, quenched with 5 mL saturated NH4Cl and diluted with 10 mL EtOAc. Separated layers, back-extracted aqueous with 3×5 mL EtOAc. Dried over Na2SO4, filtered, concentrated to give a clear, orange oil. Purified by normal-phase HPLC (40 g ISCO column, 0-50% EtOAc:Hex) to give 35-3 as a white solid.

1. customRemoved
2. temperaturecooling bath
3. temperatureCooled back to −78 C
4. customThe resulting reaction mixture
5. temperatureto slowly warm to RT
6. customwhile remaining in bath
7. waitAfter 2 h
8. customquenched with 5 mL saturated NH4Cl
9. additiondiluted with 10 mL EtOAc
10. extractionSeparated layers, back-extracted aqueous with 3×5 mL EtOAc
11. dry with materialDried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto give a clear, orange oil
15. customPurified by normal-phase HPLC (40 g ISCO column, 0-50% EtOAc:Hex)