Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 53933867, compound

HRID 1586212Notes

Reaction equation

HRID 1586212 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])=O)=[CH:5][CH:4]=1)#[N:2].C1(P(=[CH:40][C:41]([O:43][CH3:44])=[O:42])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:16]([C:15]1[CH:14]=[C:13]([C:11]([CH:10]=[CH:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:40][C:41]([O:43][CH3:44])=[O:42])[CH:20]=[CH:19][CH:18]=1)#[N:17]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 53888350HCID 53888350, compound

Product 1

HCID 53933867HCID 53933867, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Part B. 3-[3-(4-cyanophenyl)-1-oxo-2-propenyl]benzonitrile (2 gm, 7.75 mmol) was suspended in dry toluene and methyl (triphenylphosphoranylidene)acetate (2.59 gm, 7.75 mmol) added. The mixture was then heated at 100° C. for 24 hours, cooled and the solvent removed under vacuum. The residue was chromatographed on silica gel eluting ethyl acetate:hexanes (25:75, v:v) to give methyl 3-(3-cyanophenyl)-5-(4-cyanophenyl)-2,4-pentadienoate as an oil 2.1 gm (87%). MS: (M+H)+ 315; 1H NMR (CDCl3): 3.60 (s, 3H), 3.80 (s, 3H), 5.90 (s, 1H), 6.23 (m, 2H), 6.45 (d, 1H), 7.15 (d, 1H), 7.55 (m, 16H), 8.60 (d, 1H).

Workup

  1. temperaturecooled
  2. customthe solvent removed under vacuum
  3. customThe residue was chromatographed on silica gel
  4. washeluting ethyl acetate:hexanes (25:75, v:v)

Sources & evidence

ORD record
ord-2a4a145d59c1481c9d90fea73422c706
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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