Hydrochloric Acid → HCID 9822720, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-chromen-6-yl]-ethynyl]-benzoate (Compound 267, 82.0 mg, 0.188 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (120.0 mg, 3.0 mmol, 3.0 mL of a 1M aqueous solution). The resulting solution was heated to 35° C., cooled to room temperature and stirred overnight. 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 the solvent was removed under reduced pressure. The residual solid was recrystallized from CH3CN to give 65.0 mg (85%) the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.01 (2H, d, J=8.4 Hz), 7.57 (2H, d, J=8.4 Hz), 7.40 (1H, dd, J=2.0, 8.3 Hz), 7.35-7.25 (4H, m), 7.17 (1H, d, J=2.0 Hz), 6.90 (1H, d, J=8.3 Hz), 5.77 (1H,s), 2.69 (2H, q, J=7.6 Hz), 1.49 (6H, s), 1.24 (2H, t, J=7.6 Hz).

Provenance & Evidence