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

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Reaction Steps

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.

Provenance & Evidence