反応 #7922

反応方程式

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

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   温度cooled in an ice bath
2. 2
   workup.ADDITIONwas added by syringe
3. 3
   その他The cooling bath was removed
4. 4
   その他The mixture was partitioned between EtOAc (20 mL) and water (20 mL)
5. 5
   workup.ADDITIONcontaining 2N HCl (2 mL)
6. 6
   洗浄The organic phase was washed with brine (10 mL)
7. 7
   乾燥dried over MgSO4
8. 8
   ろ過filtered
9. 9
   その他evaporated under vacuum to an oil
10. 10
    その他This material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
11. 11
    洗浄The product band was eluted with 10% MeOH in CH2Cl2
12. 12
    その他the eluant evaporated under vacuum
13. 13
    その他to give an oil which

実験手順

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.

出典