Benzene → HCID 53904180, compound

HRID 1195328Notes

Reaction equation

HRID 1195328 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][CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)C=O)=[CH:4][CH:3]=1.C1(P(=[CH:44][CH:45]=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:47]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][CH:4]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH:47]=[CH:44][CH:45]=[O:46])=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14539527HCID 14539527, compound

Product 1

HCID 53904180HCID 53904180, compoundYield 89%

Procedure

To a dry mixture of 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal 0.70 g (2.1 mmoles) and triphenylphosphoranylidene acetaldehyde 0.72 g (2.5 mmoles) under argon at ambient temperature was added 20 mL of dry benzene. The suspension was warmed to reflux temperature under an argon atmosphere and the reaction was allowed to proceed at reflux temperature for 30 minutes. Analytical TLC eluted four times with 20 % ethyl acetate in hexanes (v/v) showed only one spot for product at Rf =0.15. The crude reaction mixture was poured on a silica gel column saturated with hexanes. The desired product was eluted with 1.5 liters of 20% EtOAc in hexanes (v/v) to give 0.67 g (89%) of the title compound which appears homogeneous by TLC.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureto reflux temperature under an argon atmosphere
  3. temperatureat reflux temperature for 30 minutes
  4. washAnalytical TLC eluted four times with 20 % ethyl acetate in hexanes (v/v)
  5. customThe crude reaction mixture
  6. washThe desired product was eluted with 1.5 liters of 20% EtOAc in hexanes (v/v)

Sources & evidence

ORD record
ord-8109f80d2e954dfa8571ef8c60e7f463
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

Loading…