반응 #57924

반응 방정식

sodium hydride

1-(4-tert-butyl-phenyl)-ethanone oxime

4-(2-Bromo-ethoxy)-2-hydroxy-benzoic acid methyl ester

→

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

수율 39.0%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature 1 hour
2. 2
   온도heated
3. 3
   온도at reflux 3 days
4. 4
   온도The reaction was cooled
5. 5
   기타quenched with brine
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The combined organics were washed with brine
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   농축concentrated in vacuo
10. 10
    기타The residue was purified by flash chromatography

실험 절차

To a slurry of sodium hydride (95%) (0.487 g, 20.3 mmol) in tetrahydrofuran (6 mL) was added 1-(4-tert-butyl-phenyl)-ethanone oxime (0.7021 g, 3.67 mmol) as a solution in tetrahydrofuran (18 mL) and the solution was allowed to stir at room temperature for 40 minutes. 4-(2-Bromo-ethoxy)-2-hydroxy-benzoic acid methyl ester (0.908 g, 3.64 mmol) was added as a solution in tetrahydrofuran (10 mL). The reaction was stirred at room temperature 1 hour and then heated at reflux 3 days. The reaction was cooled, quenched with brine and extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (5/95 to 10/90) afford 4-{2-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester (0.546 g, 39%) as a yellow oil which solidified on standing. mp=65.4-66.8° C.; mass spectrum (+ESI, M+H) m/z 386. 1H NMR (400 MHz, DMSO-d6); δ 10.63 (s, 1H), 7.69 (d, 1H), 7.57 (d, 2H), 7.40 (d, 2H), 6.55 (m, 2H), 4.42 (t, 2H), 4.31 (t, 2H), 3.75 (s, 3H), 2.14 (s, 3H), 1.28 (s, 9H). Elemental analysis: Calcd. for C22H27NO5: C, 68.55; H, 7.06; N, 3.63, Found: C, 68.91; H, 7.10; N, 3.60.

출처