2-Chloro-5-nitropyridine → 2-Isopropoxy-5-nitropyridine

HRID 419016ノート

反応式

HRID 419016 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([O:14][Na])([CH3:13])[CH3:12]>CC(O)C>[O:14]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH:11]([CH3:13])[CH3:12]

参加物

4

反応物 2

HCID 783082-Chloro-5-nitropyridineHCID 178459997HCID 178459997、化合物

生成物 1

HCID 120361742-Isopropoxy-5-nitropyridine収率 79.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

A freshly oven dried 500 mL round-bottom flask was charged with 2-chloro-5-nitropyridine (5.0 g, 31.6 mmol) and anhydrous iPrOH (50 mL). The resultant solution was cooled in an ice bath and iPrONa (50 mmol) in iPrOH (250 mL) added slowly, followed by stirring at the same temperature for 30 min and then at room temperature for 14 h. The reaction was quenched with H2O (5 mL), filtered through celite, and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified through automated normal-phase chromatography to afford 2-isopropoxyl-5-nitropyridine (4.6 g, 79%) which was used directly for the next step: 1H NMR (400 MHz, CDCl3) δ 9.02 (d, 1H), 8.30 (dt, 1H), 6.75 (d, 1H), 5.40 (sep, 1H), 1.38 (d, 6H); MS (ES) (M++H) expect 183.1, found 183.1.

後処理

  1. customA freshly oven dried 500 mL round-bottom flask
  2. waitat room temperature for 14 h
  3. customThe reaction was quenched with H2O (5 mL)
  4. filtrationfiltered through celite
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified

出典と根拠

ORDレコード
ord-461a6c747748489fa343df0553d0b2da
出典データセット
uspto-grants-2012_01
特許番号
US08093247B2

反応ノート

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