反应详情

A solution of (9SR,9aSR)-7-methoxy-4-methyl-9-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (38.3 mg, 0.142 mmol) in anhydrous CH2Cl2 (1.1 mL) was placed under a nitrogen atmosphere, cooled in a dry ice-acetone bath, and stirred while 1M BBr3 in CH2Cl2 (0.354 mL, 0.345 mmol) was added by syringe. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2.6 hours, then diluted with 0.2N HCl (5 mL) and EtOAc (10 mL) and shaken. The organic phase was separated, washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to a solid (35.2 mg). The crude product was purified by flash chromatography on EM silica gel 60 (230-400 mesh, 1×18 cm column) using 3:1 hexanes-EtOAc as eluting solvent, collecting 3 mL fractions. Fractions 12-26 were combined and concentrated under vacuum to approximately 1 mL of a suspension. The suspension was filtered and the solid portion washed with EtOAc and dried under vacuum to afford (9SR,9aSR)-7-hydroxy-4-methyl-9-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

1. temperaturecooled in a dry ice-acetone bath
2. additionwas added by syringe
3. customThe cooling bath was removed
4. additiondiluted with 0.2N HCl (5 mL) and EtOAc (10 mL)
5. stirringshaken
6. customThe organic phase was separated
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated under vacuum to a solid (35.2 mg)
11. customThe crude product was purified by flash chromatography on EM silica gel 60 (230-400 mesh, 1×18 cm column)
12. washas eluting solvent
13. customcollecting 3 mL fractions
14. concentrationconcentrated under vacuum to approximately 1 mL of a suspension
15. filtrationThe suspension was filtered
16. washthe solid portion washed with EtOAc
17. customdried under vacuum