Malononitrile → (2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

HRID 1397196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397196
FC(F)(F)S(O[CH2:7][C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])(=O)=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>>[F:19][C:8]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:12])[F:13])[CH2:7][CH:23]([C:22]#[N:26])[C:24]#[N:25]

Komponenten

4

Edukt 3

HCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 27758912,2,3,3,4,4,5,5-Octafluoropentyl trifluoromethanesulfonate

Produkt 1

HCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrileAusbeute 65 %

Versuchsvorschrift

A mixture of compound 5b (15.0 g, 41.2 mmol), malononitrile (5.44 g, 82.4 mmol), and potassium carbonate (28.5 g, 206 mmol) in 1,2-dimethoxymethane (150 ml) was stirred overnight at room temperature under nitrogen. The reaction mixture was quenched with water (150 ml) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were washed with brine (200 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc) to provide 2-(2,2,3,3,4,4,5,5-Octafluoropentyl)malononitrile (5c) (7.5 g, 65%) as a white solid:

Aufarbeitung

  1. customThe reaction mixture was quenched with water (150 ml)
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. washThe combined organic extracts were washed with brine (200 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-56136604385748b694f8dc9c1b1fca33
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901170B2

Notizen zur Reaktion

Wird geladen…