Benzene → HCID 53723488, compound

HRID 1086322Notes

Reaction equation

HRID 1086322 reaction equation
[C:1]([C:3](=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C=O)#[N:2].C1(P(=[CH:40][CH:41]=[O:42])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:43]1C=CC=CC=1>>[C:1]([C:3](=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)[CH:43]=[CH:40][CH:41]=[O:42])#[N:2]

Participants

4

Reactant 3

HCID 241BenzeneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14890671HCID 14890671, compound

Product 1

HCID 53723488HCID 53723488, compoundYield 100%

Procedure

To a dry mixture of 2-cyano-3,3-bis(4-fluorophenyl)-2-propenal (1.29 g, 4.8 mmol) and triphenylphosphoranylidene acetaldehyde (1.54 g, 5.04 mmol) under an inert atmosphere at ambient temperature was added 60 mL of dry benzene. The suspension was warmed to reflux temperature under an inert atmosphere and the reaction was allowed to proceed at reflux temperature for one hour. The crude reaction mixture was poured on a silica gel column saturated with hexanes. The desired product was eluted with 1 liter of hexanes followed by 1 liter of 20% ethyl acetate in hexanes (v/v) to give 1.43 g (100%) of the title compound.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureto reflux temperature under an inert atmosphere
  3. temperatureat reflux temperature for one hour
  4. customThe crude reaction mixture
  5. washThe desired product was eluted with 1 liter of hexanes

Sources & evidence

ORD record
ord-1865d8cdbfed43498130888b6263d279
Source dataset
uspto-grants-1991_07
Patent number
US05028730

Reaction notes

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