Oxygen → HCID 86630498, compound

Participants

Reaction Steps

A solution of (E)-4-fluoro-1,3-bis(4-isobutylphenyl)-4,4-bis(phenylsulfonyl) but-1-ene (5a, 506 mg, 0.818 mmol, 1.0 eq) in 20 mL of MeOH and 7 mL of CH2Cl2 was cooled to −78° C. Ozone gas generated by an ozone generator was introduced to this solution for 30 minutes, and then O2 was introduced for 5 minutes to remove excess ozone. Next, the solution was charged with NaBH4 (93.1 mg, 2.49 mmol, 3.0 eq), and the temperature was increased over two hours to room temperature. The reactant solution was then charged with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with methylene chloride and then the extract was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure by distillation, and then the reactant was purified by column chromatography (hexane:ethyl acetate=6:4) to obtain 3-fluoro-2-(4-isobutylphenyl)-3,3-bis(phenylsulfonyl)propan-1-ol as a white solid (393 mg, 98%).

Provenance & Evidence