Sodium Sulfite → HCID 86718612, compound

Participants

Reaction Steps

To a solution of 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol (529 mg, 1.38 mmol) and sodium bicarbonate (1.16 g, 13.8 mmol) in methylene chloride (40 mL) was added Dess Martin periodinane (3.00 g, 6.90 mmol) and the reaction stirred for 1 hour. The reaction mixture was poured onto a 1:1 mixture of saturated aqueous sodium sulfite solution (50 mL) and water (50 mL). The resulting mixture was extracted with ethyl acetate (150 mL). The organic phase was washed with 1 N aqueous sodium hydroxide solution (50 mL), and water (50 mL), an emulsion formed and saturated brine (100 mL) was added to separate layers. The organic phase was dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one (526 mg, 100% yield) as a white solid.

Provenance & Evidence