Реакция #2146788

Уравнение реакции

{4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester

sodium hydroxide

→

title compound

Выход 89.0%

Sodium {4-[6-Methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzo[b]furan-2-yl]-pyrazol-1-yl}-acetate

Выход 89.0%

Растворители

THF

water

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter this time the reaction was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in water (20 mL)
3. 3
   Промывкаwashed with diethyl ether (5 mL)
4. 4
   Экстракцияextracted with ethyl acetate (2×15 mL)
5. 5
   КонцентрированиеThe combined organic layers were concentrated under vacuum
6. 6
   workup.DISSOLUTIONthe residue was dissolved in methanol (2 mL)
7. 7
   workup.ADDITIONthe resulting solution was treated with a methanolic solution of sodium methoxide until a pH of 9
8. 8
   Другоеwas obtained
9. 9
   ДругоеThe solvent was removed under vacuum
10. 10
    Промывкаthe resulting yellow solid was washed with small portions of cold diethyl ether and isopropanol

Методика

To a stirred solution of {4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester (25 mg, 0.051 mmol) in a mixture of THF (1 mL) and water (1 mL) was added sodium hydroxide (70 mg, 1.75 mmol) and the reaction allowed to stir overnight at ambient temperature. After this time the reaction was concentrated under vacuum and the residue dissolved in water (20 mL) and washed with diethyl ether (5 mL). The aqueous layer was acidified to pH 1-2 with concentrated hydrochloric acid and extracted with ethyl acetate (2×15 mL). The combined organic layers were concentrated under vacuum, the residue was dissolved in methanol (2 mL) and the resulting solution was treated with a methanolic solution of sodium methoxide until a pH of 9 was obtained. The solvent was removed under vacuum and the resulting yellow solid was washed with small portions of cold diethyl ether and isopropanol to provide the title compound (22 mg, 89%). 1H-NMR (D2O) δ 7.48 (s, 1H), 7.28 (s, 1H), 6.68-6.60 (m, 2H), 6.60 (s, 2H), 6.28 (d, J=7.6 Hz, 1H), 4.49 (s, 2H), 3.61 (s, 3H), 3.49 (s, 3H), 3.39 (s, 6H).

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