Triacetoxyperiodinane → 1-(3,5-Dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-one

Participants

Reaction Steps

To a solution of 137 mg (0.29 mmol) of 1-(3,5-dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-ol (Example 12) in dichloromethane was added 350 mg (0.82 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane). After 1 hour, the reaction was quenched with saturated sodium bicarbonate, and filtered through diatomaceous earth, washing with EtOAc. The organic layer was separated and the basic aqueous phase extracted with two 5 mL portions of EtOAc. The combined organic layers were washed with 5 mL of saturated aqueous sodium bicarbonate, three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified on a prep plate (2 mm, silica gel, EtOAc-hexanes (1:9), 3×developed) to afford 84 mg (61%) of 1-(3,5-dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-one.

Provenance & Evidence