Perchloric Acid → HCID 86691563, compound

Participants

Reaction Steps

A solution of (S)-ethyl 2-(4-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (1.02 g, 2.49 mmol) in tert-butyl acetate (20 mL) was treated with 70% HClO4 (20 μL) at 23° C.). After 5 h, the reaction was added slowly over 5 min to saturated NaHCO3 (40 mL). The resulting system was extracted with DCM (3×30 mL). The 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/hexane 1:4) giving the desired product (942 mg, 81% yield). 1H NMR (400 MHz, CDCl3) δ 8.11-8.02 (m, 2H), 7.65-7.60 (m, 2H), 5.72 (s, 1H), 4.25-4.13 (m, 2H), 2.45 (d, JHF=3.2 Hz, 3H), 1.21 (s, 9H), 1.18 (t, J=7.0 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−123.1 (ap s, 1F), −73.3 (s, 3F).

Provenance & Evidence