Triacetoxyperiodinane → HCID 72546824, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 25 mL one-necked round-bottomed flask equipped with a septum and a stir bar was charged with Dess-Martin periodinane (DMP, 0.063 g, 0.15 mmol) in dry CH2Cl2 (5 mL). The solution was cooled to 0° C. in an ice bath for 10 min, compound 15b (0.045 g, 0.14 mmol) in dry CH2Cl2 (5 mL) was added and the mixture mas stirred at 0° C. for 5 min. The reaction was then warmed to rt and stirred for an additional 15 min. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 4:6). The reaction was then quenched with sat'd aq NaHCO3 solution (20 mL). The aqueous layer was extracted with Et2O (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4, gravity filtered, and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 3:7, to provide 0.031 g of the title compound as an orange solid in a 67% yield.

Provenance & Evidence