(Triphenylphosphoranylidene)acetaldehyde → 5,5-Bis(2-fluoro-4-methylphenyl)-4-(1-methyl-1H-tetrazol-5-yl)-2,4-pentadienal

HRID 330679Notes

Reaction equation

HRID 330679 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[F:26])=[C:10]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)[CH:11]=O.C1(P(=[CH:46][CH:47]=[O:48])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[F:26])=[C:10]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)[CH:11]=[CH:46][CH:47]=[O:48]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 147239943,3-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal

Product 1

HCID 542073765,5-Bis(2-fluoro-4-methylphenyl)-4-(1-methyl-1H-tetrazol-5-yl)-2,4-pentadienalYield 89.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3,3-bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal (1.35 g, 3.8 mmoles) and triphenylphosphoranylidene acetaldehyde (1.16 g, 3.8 mmoles) in benzene was heated at reflux for 3 hours. The solvent was removed and the residue purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride. The fractions containing material having Rf =0.9 [methanol-methylene chloride; 1:20 (v/v)] were combined and concentrated to give 1.3 g of the title compound; m.p.=88°-108° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was removed
  3. customthe residue purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride
  4. additionThe fractions containing material
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-061e661d2275460794776c7cf21ff1e3
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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