Sodium Hydroxide → HCID 66896009, compound

Participants

Reaction Steps

3-[3-(2-Butoxy-3,5-diisopropylphenyl)-1-methyl-1H-indol-5-yl]-but-2-enoic acid methyl ester (119 mg, 0.26 mmol) was dissolved in methanol (2.5 mL)/dioxane (2.5 mL) and treated with 1N NaOH (2.5 mL) at 60° C. for 3 h. The reaction was diluted with 1N HCl (3 mL) and extracted with ethyl acetate (3×10 mL). The combined organic portions were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to provide 134 mg of residue. The material was purified using radial chromatography by elution with hexane:ethyl acetate gradient to provide 60 mg (52%) of a light yellow solid. 1H NMR (250 MHz, CDCl3): δ 8.05 (d, 1H, J=1.4), 7.49 (dd, 1H, J=1.6, 8.7), 7.44 (s, 1H), 7.38 (d, 1H, J=8.7), 7.07 (d, J=2.3), 7.30 (d, 1H, J=2.2), 7.10 (d, 1H, J=2.2), 3.89 (s, 3H), 3.47 (m, 3H), 2.97 (sep, 2H, J=6.9), 2.73 (s, 3H), 1.46 (m, 2H), 1.34-1.22 (m, 14H), 0.78 (t, 3H, J=7.3). MS [EI+] 448 (M+H)+[EI−] 446. Anal. Calcd for C29H37NO3: C, 77.82; H, 8.33; N, 3.13. Found: C, 77.50; H, 8.28; N, 3.15.

Provenance & Evidence