(Triphenylphosphoranylidene)acetaldehyde → 3-Cyano-1-(2-formylethenyl)benzene
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].C1(P(=[CH:30][CH:31]=[O:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[CH:30][CH:31]=[O:32])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-cyanobenzaldehyde (4.5 g) in toluene (200 ml) was added (triphenylphosphoranylidene)acetaldehyde (13.6 g) and the mixture was stirred at 70° C. for 4 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane as an eluant and then the product was recrystallized from a mixture of toluene and hexane to give the desired compound (3.09 g, yield 57%) as pale yellow needle crystals.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customThe residue was purified by chromatography on a silica gel column
- customthe product was recrystallized from a mixture of toluene and hexane
Sources & evidence
- ORD record
- ord-775e35b7e2ea4900933b4d168e92ea48
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555556B1
Reaction notes
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