Potassium Hydroxide → [4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(9-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid methyl ester (0.355 g, 0.834 mmol) was reacted with 1N KOH (1.7 ml) in THF/MeOH (6 ml/4 ml) to give the product (0.261 g, 0.634 mmol, 74%) as a pale-yellow solid, mp 176-180° C. 1H NMR (DMSO-d6) δ 1.77-1.86 (m, 4H), 2.65 (t, J=5.3 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 4.69 (s, 2H), 5.33 (s, 2H), 6.96 (d, J=8.7 Hz, 2H), 7.03 (d, J=7.3 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 7.25-7.30 (m, 3H), 7.39 (d, J=8.6 Hz, 1H), 7.56 (d, J=8.7 Hz, 2H), 7.58 (d, J=1.7 Hz, 1H), 13.00 (broad s, 1H); IR (solid) 3020, 2920, 1740, 1520, 1470, and 1240 cm−1; [ESI(−)], rn/z 410 (M−H)−; Anal. Calcd. for C27H25NO3: C, 78.81; H, 6.12; N, 3.40; Found: C, 78.69; H, 6.21; N, 3.20.

Provenance & Evidence