Benzene → HCID 53954728, compound

HRID 974464Notes

Reaction equation

HRID 974464 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])=[C:20]([CH3:25])[CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)C=O)=[CH:4][C:3]=1[CH3:26].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:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([CH3:25])[CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH:49]=[CH:46][CH:47]=[O:48])=[CH:4][C:3]=1[CH3:26]

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14723917HCID 14723917, compound

Product 1

HCID 53954728HCID 53954728, compoundYield 93.3%

Procedure

To a mixture of 3,3-bis(4-fluoro-3-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal (2.12 g, 5.98 mmoles) and triphenylphosphoranylidene acetaldehyde (1.89 g, 6.22 mmoles) under an argon atmosphere was added dry benzene (26 mL). The suspension was quickly warmed to reflux under argon in an oil bath. The solids dissolved very rapidly at the reflux temperature and the color became dark brownish. The reaction was allowed to proceed at reflux temperature for a total of 60 minutes. Analytical TLC eluted ten times with 20% (v/v) ethyl acetate in hexanes showed the desired product at Rf =0.35. The crude reaction mixture was poured over a short bed of silica gel and eluted with 2 liters of 20% (v/v) ethyl acetate in hexanes to give 2.12 g (93.3%) of the title compound (TLC homogeneous). MS (CI): m/e=381 for (M+H)+ ;

Workup

  1. temperatureThe suspension was quickly warmed
  2. temperatureto reflux under argon in an oil bath
  3. dissolutionThe solids dissolved very rapidly at the reflux temperature
  4. temperatureat reflux temperature for a total of 60 minutes
  5. washAnalytical TLC eluted ten times with 20% (v/v) ethyl acetate in hexanes
  6. customThe crude reaction mixture
  7. additionwas poured over a short bed of silica gel
  8. washeluted with 2 liters of 20% (v/v) ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fc44fd8bac0f41c7a50695a1eb51defb
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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