Benzene → 5,5-bis(4-fluorophenyl)-4-(1-ethyl-1H-tetrazol-5-yl)2,4-pentadienal

HRID 974471Notes

Reaction equation

HRID 974471 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([C:12]2[N:16]([CH2:17][CH3:18])[N:15]=[N:14][N:13]=2)C=O)=[CH:4][CH:3]=1.C1(P(=[CH:45][CH:46]=[O:47])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:48]1C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([C:12]2[N:16]([CH2:17][CH3:18])[N:15]=[N:14][N:13]=2)[CH:48]=[CH:45][CH:46]=[O:47])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 147238263,3-Bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenal

Product 1

HCID 545558045,5-bis(4-fluorophenyl)-4-(1-ethyl-1H-tetrazol-5-yl)2,4-pentadienalYield 79.7%

Procedure

A solution of 3,3-bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenal (0.65 g, 1.9 mmoles) and 0.64 g (2.1 mmoles) of triphenylphosphoranylidene acetaldehyde in benzene was heated at reflux temperature for 2 hours. The solution was concentrated in vacuo and the residue purified by silica gel column chromatography eluting with CH2Cl2 to give 0.55 g (79.7%) of the title compound, m.p.=163°-165° C.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue purified by silica gel column chromatography
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-5195bde0e680414b9ceebe35b33655af
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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