Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoate

HRID 1586218Notes

Reaction equation

HRID 1586218 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(=[CH:41][C:42]([O:44][CH3:45])=[O:43])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:17]([C:16]1[CH:15]=[C:14]([C:12]([CH:11]=[CH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:41][C:42]([O:44][CH3:45])=[O:43])[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 542130173-[3-(4-Nitrophenyl)-1-oxo-2-propenyl]benzonitrile

Product 1

HCID 54059907Methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoateYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Part B. 3-[3-(4-nitrophenyl)-1-oxo-2-propenyl]benzonitrile (0.500 gm, 1.79 mmol) was suspended in toluene and methyl (triphenylphosphoranylidene)acetate (0.600 gm, 1.79 mmol) was added. The suspension was heated to reflux (at which point the solution becomes homogeneous) for 5 hrs. The reaction was cooled to room temperature and the solvent removed under vacuum. The residue was chromatographed on silica gel (20% ethyl acetate/toluene) to afford methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoate 0.441 gm (74%) as a mixture of the E/Z isomers. MS: 335(M+H)+ ; 1H NMR (CDCl3): 3.6 (s, 3H), 3.8 (s, 3H), 5.9 (s, 1H), 6.25 (m, 2H), 6.6 (d, 1H), 7.15 (m, 2H), 7.6 (m, 11H), 8.2 (d, 4H), 8.65 (d, 1H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux (at which point the solution
  3. customfor 5 hrs
  4. customthe solvent removed under vacuum
  5. customThe residue was chromatographed on silica gel (20% ethyl acetate/toluene)

Sources & evidence

ORD record
ord-29715c63e2e34ab187267791c13c0fb9
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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