Triacetoxyperiodinane → HCID 58026147, compound

Participants

Reaction Conditions

Reaction Steps

(R)-5-(4-Chloro-2-methanesulfonylphenyl)-5-methyl-3-trifluoromethylhexane-1,3-diol (27.6 g, 0.07 mol) was dissolved in methylene chloride (400 mL) with mild heating (50° C.). Dess-Martin periodinane (33.1 g, 0.08 mol) was added and the mixture was stirred at room temperature. After 1 hour the reaction was concentrated in vacuo, diluted with 300 mL of diethyl ether and filtered through a plug of CELITE® filter aid. The organic layer was washed with six 100 mL portions of saturated aqueous sodium bicarbonate solution followed by brine and drying over magnesium sulfate. The solution was filtered through CELITE® filter aid and the solvent was evaporated to give a viscous oil. The oil was dissolved in 30% Et2O/hexanes and passed through a plug of silica. Evaporation of the eluent provided (R)-5-(4-chloro-2-methanesulfonylphenyl)-3-hydroxy-5-methyl-3-trifluoromethylhexanal as a viscous oil (23.8 g, 87%).

Provenance & Evidence