تفاعل #443155

معادلة التفاعل

citric acid

( 5 )

5-Acetylamino-7,8-difluoro-1-tetralone

ethanol

sodium borohydride

→

title compound

5-Acetylamino-7,8-difluoro-1,2,3,4-tetrahydronaphthalene

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGAfter stirring for 20 minutes
2. 2
   استخلاصThe chloroform layer was extracted
3. 3
   تركيزconcentrated
4. 4
   workup.ADDITIONTo the concentrate were added 20 ml of toluene
5. 5
   درجة الحرارةby heating
6. 6
   درجة الحرارةunder reflux for 1 hour
7. 7
   workup.ADDITIONUpon addition of 100 ml of ethyl acetate
8. 8
   غسيلthe reaction product was washed with saturated brine
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    أخرىThe solvent was evaporated
11. 11
    workup.DISSOLUTIONthe residue was dissolved into a mixed solvent of 20 ml of ethanol, 20 ml of dioxane, and 0.2 ml of acetic acid
12. 12
    workup.ADDITIONThe mixture was catalytically hydrogenated with the addition of 200 mg of platinum oxide
13. 13
    أخرىThe catalyst was removed
14. 14
    تركيزthe filtrate was concentrated
15. 15
    workup.ADDITIONether was added to the concentrate

الإجراء التجريبي

The compound obtained in (5) above (1 gm) was dissolved into 20 ml of ethanol. To the solution was added 166 mg of sodium borohydride while stirring at room temperature. After stirring for 20 minutes, chloroform and 10% citric acid were added to the reaction mixture. The chloroform layer was extracted and concentrated. To the concentrate were added 20 ml of toluene and a small amount of p-TsOH, followed by heating under reflux for 1 hour. Upon addition of 100 ml of ethyl acetate, the reaction product was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dissolved into a mixed solvent of 20 ml of ethanol, 20 ml of dioxane, and 0.2 ml of acetic acid. The mixture was catalytically hydrogenated with the addition of 200 mg of platinum oxide. The catalyst was removed, the filtrate was concentrated, and ether was added to the concentrate. 0.8 gm of the title compound was obtained by collecting the precipitate by filtration.

المصدر