Hydrochloric Acid → 4-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoic acid

Participants

Reaction Steps

To a solution of ethyl 4-[[4-(5-methylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 230, 143.0 mg, 0.322 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (160.0 mg, 4.0 mmol, 4.0 mL of a 1M aqueous solution). The resulting solution was stirred overnight at room temperature. The reaction mixture was acidified with 10% aqueous HCl and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (Na2SO4) before removing the solvent under reduced pressure. The residual solid was recrystallized from CH3CN to give 110.0 mg (82%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.4 Hz), 7.63 (2H, d, J=8.3 Hz), 7.60 (1H, s), 7.44 (2H, s), 6.87 (1H, d, J=3.5 Hz), 6.79 (1H, m), 6.10 (1H, s), 2.49 (3H, s), 1.45 (6H, s).

Provenance & Evidence