HCID 21862857, compound → HCID 21862756, compound

HRID 1415769Notes

Reaction equation

HRID 1415769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[C:9]2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH:13]=[O:14])[CH:10]=[C:9]2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21862857HCID 21862857, compound

Product 1

HCID 21862756HCID 21862756, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

0.58 g (1.7 mmol) of 1-(4-fluorophenyl)-4-hydroxymethyl-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 46) was dissolved in 30 ml of methylene chloride, and 2.40 g of manganese dioxide were added to the resulting solution. The mixture was then stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was filtered using a Celite (trade mark) filter aid and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 2:3 by volume mixture of ethyl acetate and hexane, to give 0.52 g (yield 90%) of the title compound as a white powder, melting at 169-171° C.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. filtrationfilter aid
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. washeluted with a 2:3 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a05594faca834e77b58fd3d2cd315569
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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