Potassium Hydroxide → HCID 10382556, compound

Participants

Reaction Steps

To a solution of 5-(4-hydroxy-3-isopropyl-phenoxy)-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (60 mg, 0.16 mmol) in methanol/water (1:1, 3.2 mL) at room temperature was added 3N potassium hydroxide (324 μL). After stirring at room temperature for 2 hours, the mixture was diluted with water (10 mL) and washed with ethyl acetate. The aqueous solution was acidified with 1 M hydrochloric acid and then extracted with ethyl acetate (3 times 25 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford the title compound (30 mg) as a solid. 1H NMR (400 MHz, CD3OD) δ11.07 (s, 1H), 7.16 (s, 2H), 6.62 (d, 1H), 6.57 (d, 1H), 6.25-6.22 (dd, 1H), 3.24-3.19 (m, 1H), 2.27 (s, 3H), 2.17 (s, 3H), 1.12 (d, 6H). MS (APCI−) Calc: 339.1, Found: 338.2 (M−1).

Provenance & Evidence