반응 #57925

반응 방정식

4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester

sodium hydroxide

→

title compound

수율 47.0%

4-{2-[({(E)-1-[4-(tert-Butyl)-phenyl]-ethylidene}amino)oxy]-ethoxy}-2-hydroxy-benzoic Acid

수율 47.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도the reaction was heated
2. 2
   온도at reflux for 40 minutes
3. 3
   농축it was concentrated to a small volume
4. 4
   추출extracted with ethyl acetate
5. 5
   건조The combined organics were dried over anhydrous magnesium sulfate
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by flash chromatography

실험 절차

To a solution of 4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester (0.546 g, 1.29 mmol) in ethanol (10 mL) was added 1 M sodium hydroxide solution (2 mL, 2 mmol) and the reaction was heated at reflux for 40 minutes. After cooling to room temperature, it was concentrated to a small volume, acidified to pH 1 with 2M hydrochloric acid solution and extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (30/70)+1% formic acid to afford the title compound (0.224 g, 47%) as a white solid. mp=157.4-158.7° C.; mass spectrum (+ESI, M+H) m/z 372. 1H NMR (400 MHz, DMSO-d6); δ 13.60 (bs, 1H), 11.50 (bs, 1H), 7.67 (d, 1H), 7.57 (d, 2H), 7.40 (d, 2H), 6.52 (m, 2H), 4.40 (t, 2H), 4.30 (t, 2H), 2.13 (s, 3H), 1.27 (s, 9H). Elemental analysis: Calcd. for C21H25NO5: C, 67.91; H, 6.78; N, 3.77, Found: C, 67.69; H, 6.81; N, 3.68.

출처