Tetrahydro-1,4-diphenyl-1,4-epoxy-naphthalene-2,3-dicarbonitrile → 1,4-Diphenyl-2,3-dicyanonaphthalene

HRID 6611Notes

Reaction equation

HRID 6611 reaction equation
[C:1]1([C:7]23O[C:10]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([CH:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH2:12]4)[CH:9]([C:24]#[N:25])[CH:8]3[C:26]#[N:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:18]1([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([C:26]#[N:27])[C:9]=2[C:24]#[N:25])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 69257464Tetrahydro-1,4-diphenyl-1,4-epoxy-naphthalene-2,3-dicarbonitrile

Product 1

HCID 220163911,4-Diphenyl-2,3-dicyanonaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

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).

Workup

  1. customIn a dry 2 L 3-necked round bottom flask equipped with a magnetic stirring bar
  2. customwhile purging the flask with argon gas
  3. additionwas added dropwise over 2 hours
  4. stirringto stir at this temperature, and saturated ammonium chloride (300 ml)
  5. additionwas added
  6. temperatureto warm to room temperature
  7. filtrationthe white solid was filtered off
  8. customThe organic layer of the filtrate was separated
  9. washThe aqueous layer was washed with ether (100 ml)
  10. dry with materialThe combined organic layers were dried (magnesium sulfate)
  11. filtrationAfter the magnesium sulfate was filtered off
  12. customthe solvent was evaporated with a rotary evaporator
  13. customthe residue triturated with ether
  14. filtrationthe solid filtered
  15. customdried under vacuum

Sources & evidence

ORD record
ord-fe9f5420bfd84270b08f39e9fa9c1dc5
Source dataset
uspto-grants-2006_08
Patent number
US07083984B2

Reaction notes

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