Sodium Hydroxide → (E)-3-[3-(4-Fluorophenyl)-5-isopropyl-1-methyl-2-phenyl-pyrrol-4-yl]prop-2-enal

HRID 981587Notes

Reaction equation

HRID 981587 reaction equation
P(Cl)(Cl)(Cl)=O.CN([C:9]([CH:11]=[CH2:12])=[O:10])C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]([CH3:28])[C:21]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>C(#N)C.O.C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:24](/[CH:12]=[CH:11]/[CH:9]=[O:10])=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]([CH3:28])[C:21]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 17587N,N-DimethylacrylamideHCID 24813Phosphorus oxychlorideHCID 143002723-(4-Fluorophenyl)-5-isopropyl-1-methyl-2-phenyl-pyrrole

Product 1

HCID 14300273(E)-3-[3-(4-Fluorophenyl)-5-isopropyl-1-methyl-2-phenyl-pyrrol-4-yl]prop-2-enal

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent3×

Procedure

1.64 m((18 mmol) of phosphorus oxychloride are taken in 10 ml of anhydrous acetonitrile. Under argon, a solution of 1.85 g (16.8 mmol) of 90% strength dimethylaminoacrolein in 7 ml of acetonitrile is first added dropwise at -10° C. to 0° C., and a solution of 1.76 g (6 mmol) of 3-(4-fluorophenyl)-5-isopropyl-1-methyl-2-phenyl-pyrrole (Example 3) in 7 ml of acetonitrile is then added at -5° C. to 0° C. The mixture is heated under reflux overnight. It is now added to a suspension of 4.4 g of sodium hydroxide in 65 ml of water and 65 ml of toluene at 10° C. such that the temperature does not rise above 25° C. After the mixture has been stirred at room temperature for 1.5 hours, it is filtered over kieselguhr and the phases are separated.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux overnight
  3. customdoes not rise above 25° C
  4. filtrationit is filtered over kieselguhr
  5. customthe phases are separated

Sources & evidence

ORD record
ord-56494ac78bf9454b854408755393b5ef
Source dataset
uspto-grants-1991_02
Patent number
US04992462

Reaction notes

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