Sodium Hydroxide → [Isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid

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Reaction Steps

Following general procedure I and using 4-[isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester [(Compound 39, 0.15 g, contaminated with 3,3-dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 35)] and 2 mL of 5M sodium hydroxide in 10 mL of ethanol, the title compound (0.043 g, 13.4% for 2 steps) was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.86 (d, 2H, J=9.0 Hz), 6.71 (d, 1H, J=2.0 Hz), 6.64 (d, 1H, J=2.0 Hz), 6.51 (d, 2H, J=9.0 Hz), 4.36 (heptet, 1H, J=6.4 Hz), 4.30 (s, 2H), 3.09 (heptet, 1H, J=6.9 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=6.9 Hz), 1.15 (d, 6H, J=6.4 Hz).

Provenance & Evidence