Reacción #7926

Ecuación de reacción

9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

pyridine hydrochloride

→

9a-[(1E)-1-butenyl]-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Otrothe reaction mixture was partitioned between water (4 ml) and EtOAc (10 mL)
3. 3
   OtroThe organic phase was recovered
4. 4
   Lavadowashed with brine (5 mL)
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated under vacuum to an oil (30 mg)
8. 8
   OtroThe crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm)
9. 9
   Lavadoeluting with 3:1 hexanes-EtOAc
10. 10
    workup.ADDITIONThe product containing fractions
11. 11
    Concentraciónwere concentrated under vacuum

Procedimiento

A mixture of 9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (31.7 mg, 0.112 mmol) and pyridine hydrochloride (384 mg, 3.32 mmol) was placed under a nitrogen atmosphere and heated in an oil bath at 190° C. for 65 minutes. After cooling to room temperature, the reaction mixture was partitioned between water (4 ml) and EtOAc (10 mL). The organic phase was recovered, washed with brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (30 mg). The crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm), eluting with 3:1 hexanes-EtOAc. The product containing fractions were concentrated under vacuum and the residue lyophilized from benzene to provide 9a-[(1E)-1-butenyl]-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a yellow, amorphous solid.

Fuente