Potassium Hydroxide → HCID 11373710, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(1-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.184 g, 0.417 mmol) was reacted with 1N KOH (1.0 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.104 g, 0.243 mmol, 58%) as a white solid, mp 146-148° C. 1H NMR (DMSO-d6) δ 0.73 (t, J=6.8 Hz, 3H), 1.10-1.19 (m, 4H), 1.47-1.54 (m, 2H), 2.62 (t, J=7.4 Hz, 2H), 3.52 (s, 3H), 4.66 (s, 2H), 6.96 (d, J=8.9 Hz, 2H), 7.37-7.46 (m, 5H), 7.51 (t, J=7.0 Hz, 2H), 7.57 (d, J=8.9 Hz, 2H), 7.69 (d, J=1.1 Hz, 1H), 12.96 (broad s, 1H); IR (solid) 3040, 2920, 2860, 1730, 1705, 1605, 1520, 1480, 1430, 1370, and 1230 cm−1; [ESI(−)], m/z 427 (M−H)−; Anal. Calcd. for C28H29NO3.0.25H2O: C, 77.84; H, 6.77; N, 3.24; Found: C, 78.13; H, 6.60; N, 3.19.

Provenance & Evidence