Triacetoxyperiodinane → HCID 86691551, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(6-chloro-7-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (4.89 g, 10.99 mmol) in anhydrous dichloromethane (100 mL) at 0° C. was added Dess-Martin periodinane (5.59 g, 13.18 mmol) portion-wise over 5 minutes. The reaction mixture was stirred at 0° C. for 1 hour and quenched with sodium thiosulfate solution and saturated sodium bicarbonate solution and stirred for 30 minutes. The mixture was diluted with ethyl ether and washed with saturated sodium bicarbonate solution (3×), brine and dried (MgSO4), filtered, concentrated to give a yellow oil with a white precipitate. The mixture was suspended in diethyl ether, washed with brine, dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give an off-white solid (4.60 g). 1H NMR (400 MHz, CDCl3) δ: 7.93 (d, J=7.0 Hz, 1H), 7.78 (d, J=9.6 Hz, 1H), 7.67 (s, 1H), 4.41 (q, J=7.1 Hz, 2H), 2.47 (s, 3H), 1.40 (t, J=7.1 Hz, 3H).

Provenance & Evidence