Reacción #7938

Ecuación de reacción

2-propanethiol

9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

AlCl3

HCl

→

9a-BUTYL-7-HYDROXY-4-(4-HYDROXYPHENYL)-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

Disolventes

CH2Cl2

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocontained in an ice cooled flask
2. 2
   workup.STIRRINGThe resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours
3. 3
   workup.STIRRINGstirred for 15 minutes at room temperature
4. 4
   OtroThe EtOAc layer was separated
5. 5
   Lavadowashed with 1N HCl and brine
6. 6
   Secadodried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated under vacuum
9. 9
   Otroto give a yellow gum
10. 10
    OtroThis material was triturated with benzene
11. 11
    Otroto give
12. 12
    Filtraciónafter filtration
13. 13
    Secadodrying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid

Procedimiento

An ice-cold solution of 9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg, 0.08 mmol) in anhydrous CH2Cl2 (1 mL) was added to AlCl3 (96 mg, 0.72 mmol) contained in an ice cooled flask. The mixture was stirred at 0° C. under a nitrogen atmosphere and treated with 2-propanethiol (0.056 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours, then treated with ice (approx. 2 mL), 2N HCl (2 mL) and EtOAc (4 mL) and stirred for 15 minutes at room temperature. The EtOAc layer was separated, washed with 1N HCl and brine, dried over MgSO4, filtered, and evaporated under vacuum to give a yellow gum. This material was triturated with benzene to give, after filtration and drying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid.

Fuente