반응 #7974
ord-7dd6343aeafb46f08ecf5adfe3390eb6
반응 방정식
반응 조건
후처리
- 1온도cooled in a dry ice-acetone bath
- 2workup.ADDITIONwas added by syringe
- 3기타The cooling bath was removed
- 4workup.ADDITIONdiluted with 0.2N HCl (5 mL) and EtOAc (10 mL)
- 5workup.STIRRINGshaken
- 6기타The organic phase was separated
- 7세척washed with brine
- 8건조dried over MgSO4
- 9여과filtered
- 10기타evaporated under vacuum to a solid (35.2 mg)
- 11기타The crude product was purified by flash chromatography on EM silica gel 60 (230-400 mesh, 1×18 cm column)
- 12세척as eluting solvent
- 13기타collecting 3 mL fractions
- 14농축concentrated under vacuum to approximately 1 mL of a suspension
- 15여과The suspension was filtered
- 16세척the solid portion washed with EtOAc
- 17기타dried under vacuum
실험 절차
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.