Benzene → 5,5-Bis(4-fluorophenyl)-4-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-2,4-pentadienal

HRID 330688Notes

Reaction equation

HRID 330688 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[C:9]([C:12]2[N:13]=[N:14][N:15]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:16]=2)C=O)=[CH:4][CH:3]=1.C1(P(=[CH:62][CH:63]=[O:64])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:65]1C=CC=CC=1>>[F:42][C:39]1[CH:40]=[CH:41][C:36]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:9]([C:12]2[N:13]=[N:14][N:15]([C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:16]=2)[CH:65]=[CH:62][CH:63]=[O:64])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14723828HCID 14723828, compound

Product 1

HCID 542748325,5-Bis(4-fluorophenyl)-4-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-2,4-pentadienal

Procedure

To a solution of 1.75 g (3.15 mmol) 3,3-bis(4-fluorophenyl)-2-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-2-propenal in 50 mL of dry benzene was added 0.96 g (3.15 mmol) triphenylphosphoranylidene acetaldehyde and the solution heated at reflux for 96 hours. The solution was concentrated in vacuo and the residue purified by chromatography on alumina (Alcoa Chemicals, grade F-20) eluting with 10% ethyl acetate in hexane to give upon concentration of the appropriate fractions 0.95 g of the title compound; m.p.=122°-124° C.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 96 hours
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue purified by chromatography on alumina (Alcoa Chemicals, grade F-20)
  5. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-128bee0a5f574a85971e9c13dca0bf23
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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