Hydrochloric Acid → HCID 21846702, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)thiochromen-6-yl]-ethynyl]-benzoate (Compound 226, 126.0 mg, 0.287 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (160.0 mg, 4.0 mmol, 2.0 mL of a 2M aqueous solution). The resulting solution was heated to 45° C. and stirred overnight. Upon cooling to 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 85.0 mg (72%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.00 (2H, d, J=8.3 Hz), 7.58 (2H, d, J=8.3 Hz), 7.45-7.38 (2H, m), 7.28-7.17 (5H, m), 5.92 (1H, s), 2.37 (3H, s), 1.47 (6H, s).

Provenance & Evidence