Sodium Hydroxide → 3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid

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Reaction Steps

3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester (74 mg, 0.126 mmol) was dissolved in methanol (1 mL)/dioxane (1 mL) and treated with 1N NaOH (1 mL, 1 mmol) at 60° C. for 2 h. The reaction was diluted with 1N HCl (3 mL)/water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic portions were washed with water (10 mL), brine (10 mL), dried (MgSO4), filtered and evaporated in vacuo to provide 78 mg of a yellow oil. The material was purified using radial chromotagraphy with a gradient of hexane/ethyl acetate to provide 42 mg (58%) of a yellow amorphous foam. 1H NMR (250 MHz, CDCl3): δ 8.08 (d, 1H, 8.2),7.58 (m, 2H), 7.42-7.21 (m, 5H), 7.03 (d, 1H, J=2.2), 6.82 (d, 1H, J=2.2), 6.49 (s, 1H), 6.00 (bs, 1H), 3.28 (sep, 1H, J=6.9), 2.96 (t, 2H, J=6.0), 2.81 (sep, 1H, J=6.9), 1.18 (d 6H, J=6.9), 1.17 (d, 6H, J=6.9). MS [EI+] 574, (M+H)+, [EI−] 572 (M−H)+.

Provenance & Evidence