Sodium Carbonate → 1-(4-Fluorophenyl)-5-formyl-2-(4-methylsulfonylphenyl)pyrrole

HRID 1415768Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:28](=O)([O-])[O-:29].[Na+].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:28]=[O:29])=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.67 g (5.3 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) were dissolved in 30 ml of dimethylformamide, 0.50 ml (5.3 mmol) of phosphorous oxychloride was added to the resulting solution, and the mixture was then stirred at 60° C. for 2 hours. At the end of this time, the reaction mixture was gradually added to ice-water and the pH of the mixture was adjusted to a value of 8-9 by the addition of sodium carbonate. The mixture was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 5:1 by volume mixture of hexane and ethyl acetate, to give 0.90 g (yield 50%) of the title compound as a white powder, melting at 135-137° C.

Workup

extractionThe mixture was then extracted with ethyl acetate
extractionThe organic extract
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
customafter which the solvent was removed by distillation under reduced pressure
washeluted with a 5:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record: ord-69481f5ca3c64a0d98308cd79adb7d12
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05908858

Reaction notes

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