4-Cyanobenzaldehyde → 1,3-bis(4-cyanophenyl)prop-2-en-1-one

HRID 365940Notes

Reaction equation

HRID 365940 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:11]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)(=O)[CH3:12]>CO>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7](=[O:8])[CH:12]=[CH:11][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 740444'-Cyanoacetophenone

Product 1

HCID 46180931,3-bis(4-cyanophenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The synthesis employed for the 2,4-substituted dicationic furans 1-6 used 2,4-bis(4-cyanophenyl)furan as the key intermediate and is outlined in scheme 1. This key compound was obtained through a four step approach. A base catalyzed Aldol condensation between 4-cyanobenzaldehyde and 4-acetylbenzonitrile in methanol gave 1,3-bis(4-cyanophenyl)prop-2-en-1-one. Bromination of the double bond of the chalcone (i) in CHCl3 yielded 1,3-bis(4-cyanophenyl)-2,3-dibromopropan-1-one (ii), which was reacted with 2.5 equivalent of MeONa in MeOH to form 1,3-bis(4-cyanophenyl)-3-methoxyprop-2-en-1-one (iii) (Weygand, C.; Bauer, E.; Hennig, H., Ueber Beziehungen zwischen Polymorphismus und Ethylen-Stereomerie. B. 1929, 62, 562-573). The reaction of dimethylsulfonium methylide with the enolether (iii) gave 2,4-disubstituted furan (iv) (Harris, C. M. et al., J. Org. Chem. 1974, 39, 72-77).

Workup

  1. customThis key compound was obtained through a four step approach

Sources & evidence

ORD record
ord-c965e4556e4e4b3a95b88b87803800f6
Source dataset
uspto-grants-2000_10
Patent number
US06127554

Reaction notes

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