Reacción #443152

Ecuación de reacción

potassium permanganate

magnesium sulfate

( 6 )

5-Acetylamino-7-fluoro-1,2,3,4-tetrahydronaphthalene

water

→

title compound

8-Acetylamino-6-fluoro-1-tetralone

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction product was extracted 3 times with chloroform
2. 2
   LavadoThe chloroform layer was washed with water and saturated brine in this order
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   OtroThe solvent was evaporated
5. 5
   Otroto obtain fractions
6. 6
   workup.ADDITIONcontaining the target compound
7. 7
   ConcentraciónThe fractions were concentrated

Procedimiento

To a solution of the compound obtained in (6) above (9.46 gm) in 420 ml of acetone was added 42 ml of 15% aqueous solution of magnesium sulfate. After cooling to 0° C., 21.7 gm of potassium permanganate was added to the mixture, a bit at a time. The mixture was stirred for 50 minutes at 0° C. and for 1 hour at room temperature. Upon addition of 1 l of water, the reaction product was extracted 3 times with chloroform. The chloroform layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (3:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 7.98 gm of the title compound.

Fuente