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

HRID 1050133

반응식

HRID 1050133 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1)[CH3:2].CC(OC(C)=O)=[O:13]>>[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 72.2%

반응 조건

온도
25 °C

실험 절차

A mixture of 4-ethoxypyridine 1-oxide (20 g, 144 mmol) in Ac2O (200 mL, 7.836 mol) was heated to refluxed for 4 h. Then, the solvent was removed in vacuo, and the residue was dissolved in MeOH (50 mL) and water (50 mL) and stirred at 25° C. for 16 h. The mixture was then concentrated and 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 (17 g, 104 mmol, 72% yield). 1H NMR (400 MHz, MeOH-d4) δ 8.20 (d, J=7.6 Hz, 2H), 7.12 (d, J=7.6 Hz, 2H), 4.18 (q, J=7.2 Hz, 2H), 1.42 (t, J=6.8 Hz, 3H); ES-LCMS m/z: 140.0 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureto refluxed for 4 h
  3. customThen, the solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in MeOH (50 mL)
  5. concentrationThe mixture was then concentrated
  6. customthe crude material was purified by silica column chromatography (DCM/MeOH=10:1)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9987eea31ef4421fb8741ebdaec8e82b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382238B2

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