Benzaldehyde → 2-Benzylidene-but-3-ynenitrile
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture was heated
- temperatureat reflux overnight
- temperatureThe reaction was cooled
- customevaporated
- customthen purified by flash column chromatography
- washeluting with 1:9 ethyl acetate/hexane
- additionthe product containing fractions
- customevaporated
Sources & evidence
- ORD record
- ord-2eb7446550e549a78eee17324161b795
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745638B2
Reaction notes
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