Reacción #7922

Ecuación de reacción

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

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente