Triacetoxyperiodinane → HCID 18448167, compound

Participants

Reaction Steps

A solution of 4.2 g of 4-bromobutyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 50 mL of dichloromethane was treated with 4.2 g of Dess-Martin reagent for 1 h at rt. The reaction was quenched by 0.5 mL of water and stirred at rt for 1 h, filtered, and evaporated. The residue was dissolved in a solvent mixture of 30 mL of THF and 30 mL of t-BuOH, and treated with 50 mL of 1 M of H3PO4 and 25 mL of 1 M of NaClO2 in the presence of 5 mL of 2-methyl-2-butene. The resulting mixture was stirred at rt for 15 min; the organic layer was separated, washed with brine, dried (Na2SO4), and evaporated to afford 4 g of the crude acid for further use.

Provenance & Evidence