Reaktion #706820

Reaktionsgleichung

ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate

Compound 231

Ethyl 4-[[4-(2-ethyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate

NaOH

HCl

→

title compound

Ausbeute 73.7%

4-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acid

Ausbeute 73.7%

Lösungsmittel

THF

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   WaschenThe combined organic layers were washed with H2O, saturated aqueous NaCl
3. 3
   Trocknendried (Na2SO4)
4. 4
   Sonstigebefore removing the solvent under reduced pressure
5. 5
   SonstigeThe residual solid was recrystallized from CH3CN

Vorschrift

To a solution of ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 231, 23.0 mg, 0.05 mmol) in 1.0 mL THF and 1.0 mL EtOH was added NaOH (40.0 mg, 1.0 mmol, 1.0 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 15.5 mg (72%) of the title compound as an orange solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz), 7.61 (1H, s), 7.44 (2H, s), 6.90 (1H, d, J=3.5 Hz), 6.83 (1H, d, J=3.5 Hz), 6.10 (1H, s), 2.86 (2H, q, J=7.6 Hz), 1.45 (6H, s), 1.30 (3H, t, J=7.6 Hz).

Quelle