Perchloric Acid → (S)-ethyl 2-tert-butoxy-2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Participants

Reaction Steps

To a solution of (S)-ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (3.80 g, 9.35 mmol) in tert-butyl acetate (94 mL) was added 70% perchloric acid (0.160 mL, 1.37 mmol). The reaction mixture was stirred for 5 h and quenched with solid sodium bicarbonate. The mixture was stirred for 5 minutes and saturated sodium bicarbonate solution was carefully added until pH 7, then diluted with water and extracted with ethyl acetate (2×). The combined organic layer was washed with saturated sodium bicarbonate solution and dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 25% ethyl acetate/hexanes) to give the desired product. 1H NMR (400 MHz, CDCl3) δ 8.08 (dd, J=8.7, 8.7 Hz, 2H), 7.63-7.55 (m, 2H), 5.75 (s, 1H), 4.3-4.1 (m, 2H), 2.63 (s, 3H), 2.47 (s, 3H), 1.20 (s, 3H), 1.17 (t, J=7.4 Hz, 3H).

Provenance & Evidence