반응 #7922

반응 방정식

9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

BBr3

benzene

→

9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   workup.ADDITIONwas added by syringe
3. 3
   기타The cooling bath was removed
4. 4
   기타The mixture was partitioned between EtOAc (20 mL) and water (20 mL)
5. 5
   workup.ADDITIONcontaining 2N HCl (2 mL)
6. 6
   세척The organic phase was washed with brine (10 mL)
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   기타evaporated under vacuum to an oil
10. 10
    기타This material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
11. 11
    세척The product band was eluted with 10% MeOH in CH2Cl2
12. 12
    기타the eluant evaporated under vacuum
13. 13
    기타to give an oil which

실험 절차

A solution of 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (76 mg, 0.267 mmol) in anhydrous CH2Cl2 (2 mL) was placed under a nitrogen atmosphere, cooled in an ice bath, and stirred while 1M BBr3 in CH2Cl2 (0.80 mL, 0.80 mmol) was added by syringe. The cooling bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was partitioned between EtOAc (20 mL) and water (20 mL) containing 2N HCl (2 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil. This material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate using 5% MeOH in CH2Cl2 as the developing solvent. The product band was eluted with 10% MeOH in CH2Cl2 and the eluant evaporated under vacuum to give an oil which was lyophilized from benzene to afford 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

출처