Triacetoxyperiodinane → HCID 23592303, compound

Participants

Reaction Steps

To a solution of Dess-Martin periodinane (4.24 g, 10.0 mmol) in dichloromethane (100 mL) at 0° C. was added dropwise 4-chloro-N-(2,5-dichlorophenyl)-N-(1R)(4-hydroxy-1-methylbutyl)benzenesulfonamide (3.60 g, 8.8 mmol) in dichloromethane (50 mL). The reaction was allowed to slowly come to room temperature with stirring over 18 h. The reaction was then quenched with a saturated solution of 1:1 NaHCO3/NaHSO3 (25 mL) and diluted with EtOAc. The organic phase was washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. Flash silica gel chromatography (silica gel, 20% EtOAc/hexanes) of the concentrate afforded the title compound as a white wax (1.85 g, 51% yield): 1H NMR (CDCl3) δ 9.70 (s, 1H), 7.68–7.75 (m, 2H), 6.98–7.49 (m, 5H), 4.80–4.85 (m, 1H), 2.36–3.00 (m, 2H), 1.17–1.36 (m, 3H).

Provenance & Evidence