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

HRID 1050133

反応式

HRID 1050133 の反応式
[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]

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 2524794-Ethoxypyridine n-oxide

生成物 1

HCID 1784669604-ethoxy-1H-pyridin-2-one収率 72.2%

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9987eea31ef4421fb8741ebdaec8e82b
出典データセット
uspto-grants-2016_07
特許番号
US09382238B2

関連ノート

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