Sodium Thiosulfate → HCID 86691561, compound

Participants

Reaction Steps

A solution of ethyl 2-(4-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (˜1.54 g, 3.76 mmol) in DCM (60 mL) was treated with Dess-Martin periodinane (1.91 g, 4.51 mmol) at 23° C. After 4 h, the orange reaction was slowly added to 10% Na2S2O3 (28 mL) at 23° C. After 5 min of stirring, the reaction was diluted with H2O (40 mL) and extracted with DCM (3×20 mL). Combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was dissolved in benzene. The solution was wet-loaded onto a 40 g “gold” ISCO silica gel column and purified by flash chromatography (hexane→ethyl acetate/hexanes 1:4) giving the desired product (1.08 g, 70% yield over 2 steps from ethyl 2-tert-butoxy-2-(4-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate). 1H NMR (400 MHz, CDCl3) δ 8.16-8.08 (m, 2H), 7.76-7.68 (m, 2H), 4.41 (q, J=7.1 Hz, 2H), 2.39 (d, JHF=3.2 Hz, 3H), 1.40 (t, J=7.1 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−122.3 (app. s, 1F), −73.3 (s, 3F).

Provenance & Evidence