4-Nitropyridine N-oxide → 4-Ethoxypyridine n-oxide

HRID 576148

반응식

HRID 576148 반응식
[N+]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][CH:5]=1)([O-])=O.[CH2:11]([O-:13])[CH3:12].[Na+]>C1COCC1>[CH2:11]([O:13][C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][CH:5]=1)[CH3:12]

참가 물질

4

반응물 2

HCID 143004-Nitropyridine N-oxideHCID 2723922Sodium ethoxide

생성물 1

HCID 2524794-Ethoxypyridine n-oxide수율 45.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a mixture of 4-nitropyridine 1-oxide (50 g, 357 mmol) in THF (500 mL) was added sodium ethanolate (48.6 g, 714 mmol). The mixture was stirred at 25° C. for 16 h. The reaction residue was concentrated. The crude material was purified by silica column chromatography (DCM/MeOH=25:1). All fractions found to contain product by TLC (DCM/MeOH=25:1, Rf=0.6) were combined and concentrated to yield a dark red solid of 4-ethoxypyridine 1-oxide (25 g, 162 mmol, 45.3% yield): 1H NMR (400 MHz, CD3OD) δ 8.20-8.18 (m, 2H), 7.11-7.10 (m, 2H), 4.21-4.15 (m, 2H), 1.42 (t, J=7.2 Hz, 3H); ES-LCMS m/z 140.0 (M+H).

후처리

  1. concentrationThe reaction residue was concentrated
  2. customThe crude material was purified by silica column chromatography (DCM/MeOH=25:1)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-549991cb8fbb44e1a2320dbea733630b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035063B2

연결된 노트

불러오는 중…