Reacción #7945

Ecuación de reacción

9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

BBr3

→

solid

Rendimiento 99.1%

9a-butyl-7-hydroxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Rendimiento 99.1%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise by syringe
2. 2
   OtroThe cooling bath was removed
3. 3
   workup.ADDITIONThe mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL)
4. 4
   workup.STIRRINGshaken vigorously
5. 5
   OtroThe EtOAc layer was separated
6. 6
   Lavadowashed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL)
7. 7
   Secadodried over MgSO4
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated under vacuum

Procedimiento

A solution of 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28.4 mg, 0.1 mmol) in anhydrous CH2Cl2 (1.7 mL) was stirred under a nitrogen atmosphere and cooled in a dry ice-acetone bath while 1M BBr3 in CH2Cl2 (0.30 mL, 0.3 mmol) was added dropwise by syringe. The cooling bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL) and shaken vigorously. The EtOAc layer was separated, washed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL), dried over MgSO4, filtered and evaporated under vacuum to give an ochre solid (26.8 mg). The crude product was suspended in CDCl3 (1 mL) and filtered. The solid portion was dried under vacuum to afford 9a-butyl-7-hydroxy-8-methyl-1,2,9,9a-3H-tetrahydro-fluoren-3-one as an olive colored powder.

Fuente