Reacción #576135

Ecuación de reacción

3,9-dimethylpentacene-5,7(12H,14H)-dione

→

2,10-dimethylpentacene

Disolventes

2-methoxyethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroflushed with nitrogen for 15 minutes
2. 2
   workup.ADDITIONTo this was added 0.948 grams of sodium borohydride
3. 3
   workup.STIRRINGstirring
4. 4
   workup.ADDITIONTo the mixture was added 6.3 mL of methanol
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 1.5 hours at room temperature
7. 7
   workup.ADDITIONTo the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid
8. 8
   workup.STIRRINGThe mixture was stirred for one hour at room temperature
9. 9
   workup.ADDITIONTo the mixture was added 50 mL of water
10. 10
    Otrothe resulting solid was isolated by filtration
11. 11
    Lavadowashed with water
12. 12
    LavadoThe solid was washed with tetrahydrofuran until a pale filtrate
13. 13
    Otroresulted
14. 14
    LavadoThe solid was washed with heptane
15. 15
    Otrodried under an atmosphere of nitrogen

Procedimiento

A mixture of 1 gram of 3,9-dimethylpentacene-5,7(12H,14H)-dione and 10 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 0.948 grams of sodium borohydride and stirring was continued at room temperature overnight. To the mixture was added 6.3 mL of methanol and stirring was continued for 1.5 hours at room temperature. To the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid. The mixture was stirred for one hour at room temperature followed by heating for one hour at 60° C. To the mixture was added 50 mL of water and the resulting solid was isolated by filtration and washed with water. The solid was washed with tetrahydrofuran until a pale filtrate resulted. The solid was washed with heptane and dried under an atmosphere of nitrogen to give 2,10-dimethylpentacene.

Fuente