Sodium borohydride → 1-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

HRID 1585081Notes

Reaction equation

HRID 1585081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH:23]=[O:24])=[C:9]2[CH3:25])=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][OH:24])=[C:9]2[CH3:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108321701-(4-Fluorophenyl)-4-formyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 105463821-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrroleYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxaldehyde (Example 18) (1.4 g, 3.9 mmol) in EtOH (30 ml), sodium borohydride (297 mg, 7.84 mmol) was added. After heating at reflux for 3 hours, the reaction mixture was cooled to room temperature and quenched with acetic acid. The solvent was removed under reduced pressure and the residue was redissolved in methylene chloride. After washing with 1N HCl and brine, the organic fractions were filtered, concentrated and purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-methanol (1.4 g, 100%) as a white solid: mp (DSC) 148° C. Anal Calc'd. for C19H18NSFO3 ·0.4 H2O: C, 62.25; H, 5.17; N, 3.82; S, 8.75. Found: C, 62.29; H, 4.87; N, 3.86; S, 8.86.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3 hours
  3. customquenched with acetic acid
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was redissolved in methylene chloride
  6. washAfter washing with 1N HCl and brine
  7. filtrationthe organic fractions were filtered
  8. concentrationconcentrated
  9. custompurified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-0c38e840949848a0b661f6ea91c3a4c4
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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