Benzaldehyde → 2-Benzylidene-but-3-ynenitrile

HRID 132054

Reaction equation

HRID 132054 reaction equation
[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

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 702EthanolHCID 8010Malononitrile

Product 1

HCID 860306562-Benzylidene-but-3-ynenitrile

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-396fc1aa677b473c8ea1937ac30b2b83
Source dataset
uspto-grants-2008_06
Patent number
US07385059B2

Linked notes

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