Benzaldehyde → 2-Benzylidene-but-3-ynenitrile

HRID 20316

Reaktionsgleichung

Reaktionsgleichung von HRID 20316
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#N.[CH2:14](O)C>N1CCCCC1>[CH:1](=[C:10]([C:11]#[CH:14])[C:9]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 702EthanolHCID 8010Malononitrile

Produkt 1

HCID 860306562-Benzylidene-but-3-ynenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8082PiperidineKatalysator

Versuchsvorschrift

To a solution of benzaldehyde (2 g; 18.9 mmol) and malononitrile (1.37 g; 20.7 mmol) in ethanol (40 ml) was added 5 drops of piperidine and the mixture was heated at reflux overnight. The reaction was cooled, evaporated then purified by flash column chromatography eluting with 1:9 ethyl acetate/hexane and the product containing fractions combined and evaporated to give 930 mg of 2-benzylidene-but-3-yne nitrile.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction was cooled
  4. customevaporated
  5. customthen purified by flash column chromatography
  6. washeluting with 1:9 ethyl acetate/hexane
  7. additionthe product containing fractions
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2eb7446550e549a78eee17324161b795
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745638B2

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