Reaction #6707

Reaction equation

tetrahydro-1,4-diphenyl-1,4-epoxy-napthalene-2,3-dicarbonitrile

→

1,4-diphenylnaphthalene-2,3-di-carbonitrile

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherIn a dry 2 L 3-necked round bottom flask equipped with a magnetic stirring bar
2. 2
   Otherwhile purging the flask with argon gas
3. 3
   workup.ADDITIONwas added dropwise over 2 hours
4. 4
   workup.STIRRINGto stir at this temperature, and saturated ammonium chloride (300 ml)
5. 5
   workup.ADDITIONwas added
6. 6
   Temperatureto warm to room temperature
7. 7
   Filtrationthe white solid was filtered off
8. 8
   OtherThe organic layer of the filtrate was separated
9. 9
   WashThe aqueous layer was washed with ether (100 ml)
10. 10
    DryingThe combined organic layers were dried (magnesium sulfate)
11. 11
    FiltrationAfter the magnesium sulfate was filtered off
12. 12
    Otherthe solvent was evaporated with a rotary evaporator
13. 13
    Otherthe residue triturated with ether
14. 14
    Filtrationthe solid filtered
15. 15
    Otherdried under vacuum

Procedure

In a dry 2 L 3-necked round bottom flask equipped with a magnetic stirring bar, dropping funnel, gas inlet tube attached to an argon gas cylinder, was placed tetrahydro-1,4-diphenyl-1,4-epoxy-napthalene-2,3-dicarbonitrile (20 g) and dry tetrahydrofuran (450 ml) while purging the flask with argon gas. The mixture was stirred for 20 minutes. The flask was cooled to −78° C. (acetone/dry ice) and Lithium bis(trimethylsilyl)- amide (150 ml, 1.0 M THF) was added dropwise over 2 hours. The mixture was allowed to stir at this temperature, and saturated ammonium chloride (300 ml) was added. The mixture was allowed to warm to room temperature, and the white solid was filtered off. The organic layer of the filtrate was separated. The aqueous layer was washed with ether (100 ml). The combined organic layers were dried (magnesium sulfate). After the magnesium sulfate was filtered off, the solvent was evaporated with a rotary evaporator, the residue triturated with ether, and the solid filtered, dried under vacuum and weighed (17 g).

Source