Sodium Hydroxide → [2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid

Participants

Reaction Steps

To a stirred solution of 0.44 g (0.97 mmol) of 23 in 7 mL of MeOH and 7 mL of THF was added 1.5 mL (1.5 mmol) of 1 N NaOH solution. The resulting solution was stirred at room temperature for 4 h. The solvent was removed in vacuo, and the residue was diluted with 10 mL of H2O, acidified to pH˜3 with 1N HCl, and extracted with 30 mL of EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:1) to afford 0.36 g (87%) of 8: mp 238-240° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.5 (brs, 1H), 12.04 (s, 1H), 8.00 (s, 1H), 7.93 (d, J=7.4 Hz, 2H), 7.80 (s, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.59-7.48 (m, 9H), 7.38 (t, J=7.1 Hz, 1H), 7.07 (d, J=1.2 Hz, 1H), 3.69 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 186.6, 172.0, 147.4, 141.6, 141.0, 136.3, 132.6, 132.2, 131.9, 131.4, 130.4, 129.2, 129.1, 128.8, 128.3, 125.6, 125.4, 120.5, 99.3, 34.1; IR (KBr) cm−1 3417, 3054, 1713, 1596.

Provenance & Evidence