Acetic Anhydride → 4-ethoxy-1H-pyridin-2-one

HRID 1049990

반응식

HRID 1049990 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1)[CH3:2].C(OC(=O)C)(=[O:13])C>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([OH:13])[CH:5]=1)[CH3:2]

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 2524794-Ethoxypyridine n-oxide

생성물 1

HCID 1784669604-ethoxy-1H-pyridin-2-one수율 45%

반응 조건

온도
25 °C

실험 절차

A mixture of 4-ethoxypyridine 1-oxide (5 g, 35.9 mmol) in acetic anhydride (36.7 g, 359 mmol) was heated to reflux for 4 h. Then the solvent was removed in vacuo, and the residue was dissolved in MeOH (25 mL) and H2O (25 mL) and stirred at 25° C. for 16 h. The mixture was concentrated. The crude material was purified by silica column chromatography (DCM/MeOH=10:1). All fractions found to contain product by TLC (DCM/MeOH=10:1, Rf=0.6) were combined and concentrated to yield a dark yellow solid of 4-ethoxypyridin-2-ol (2.5 g, 16.17 mmol, 45.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.28 (d, J=7.6 Hz, 1H), 6.07 (d, J=3.2, 7.2 Hz, 1H), 5.86-7.85 (d, J=2.4 Hz, 1H), 4.06-4.01 (m, 2H), 1.38 (t, J=7.2 Hz, 3H); ES-LCMS m/z 140.0 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThen the solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in MeOH (25 mL)
  5. concentrationThe mixture was concentrated
  6. customThe crude material was purified by silica column chromatography (DCM/MeOH=10:1)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2bff313415e74ec18d9e8ddaf6503d7b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382238B2

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