Sodium Thiosulfate → HCID 86691571, compound

Participants

Reaction Steps

A solution of ethyl 2-(4-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (crude, 1.22 g, ˜2.60 mmol) in DCM (60 mL) was treated with Dess-Martin periodinane (1.32 g, 3.12 mmol) at 23° C. After 30 min, 10% Na2S2O3 (30 mL) was added at 23° C. The system was diluted with H2O (20 mL) and extracted with DCM (3×30 mL). Combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene, filtered, and wet-loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product (1.18 g, 98% yield over 2 steps from ethyl 2-(4-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=8.6 Hz, 1H), 8.13 (d, J=8.2 Hz, 1H), 7.77 (dd, J=8.6, 8.2 Hz, 1H), 7.71 (dd, J=8.6, 8.6 Hz, 1H), 4.42 (q, J=7.0 Hz, 2H), 2.57 (s, 3H), 1.39 (t, J=7.0 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−73.3 (s).

Provenance & Evidence