Benzene → HCID 53912652, compound

HRID 330674Notes

Reaction equation

HRID 330674 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[CH3:25])=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)C=O)=[C:4]([CH3:26])[CH:3]=1.C1(P(=[CH:46][CH:47]=[O:48])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:49]1C=CC=CC=1>>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:26])=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH:49]=[CH:46][CH:47]=[O:48])=[C:19]([CH3:25])[CH:20]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14723984HCID 14723984, compound

Product 1

HCID 53912652HCID 53912652, compound

Procedure

A solution of 3,3-bis(4-fluoro-2-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal (0.88 g, 2.5 mmoles) and triphenylphosphoranylidene acetaldehyde (0.75 g, 2.5 mmoles) in benzene (50 mL) was heated at reflux for 3 hours. The solvent was removed by evaporation and the crude 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 [1:20 (v/v) methanolmethylene chloride] were combined and concentrated to give 0.8 g of the title compound; m.p.=75°-95° C. MS: M+ =380;

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was removed by evaporation
  3. customthe crude 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-2f0578558ef146b59f8dee58adfae33a
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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