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

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 1 of example 4. Thus, 4-(9-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol (0.419 g, 1.185 mmol) was reacted with K2CO3 (0.213 g, 1.541 mmol) and methyl bromoacetate (0.236 g, 1.541 mmol) in acetone to give the product (0.362 g, 0.851 mmol, 72%) as a white solid, mp 109-112° C. 1H NMR (DMSO-d6) δ 1.77-1.87 (m, 4H), 2.65 (t, J=5.3 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 3.71 (s, 3H), 4.81 (s, 2H), 5.33 (s, 2H), 6.98 (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=8.4 Hz, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.58 (d, J=1.1 Hz, 1H); [ESI(+)], m/z 426 (M+H)+.

Provenance & Evidence