Methanol → Methyl 2-(6-chloro-2-methoxypyridin-3-yl)propanoate

HRID 922570

反応式

HRID 922570 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]([CH3:13])[C:11]#N)=[CH:4][CH:3]=1.[CH3:14][OH:15].Cl.C[OH:18]>>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]([CH3:13])[C:11]([O:15][CH3:14])=[O:18])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 21893726Hydrochloride methanolHCID 1179928772-(6-Chloro-2-methoxypyridin-3-yl)propanenitrile

生成物 1

HCID 117992989Methyl 2-(6-chloro-2-methoxypyridin-3-yl)propanoate収率 67%

実験手順

To a stirred solution of 2-(6-Chloro-2-methoxypyridin-3-yl)propanenitrile (1850 g, 9439 mmol) in MeOH (20 L) was added MeOH/HCl (about 2 M) at r.t. After the addition, the resulting mixture was heated at reflux for 12 hours. The reaction mixture was evaporated to move most of MeOH, and the residue was diluted with H2O (6 L) and basified to pH=9˜10 with solid NaHCO3. The aqueous layer was extracted with CH2Cl2 (15 L). The organic layer was washed with water (10 L) and brine (10 L), dried over Na2SO4 and concentrated to dryness. The crude residue was purified by column chromatography (petroleum ether/EtOAc=100:0˜80:20) to afford methyl 2-(6-chloro-2-methoxypyridin-3-yl)propanoate (1450 g, 67%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.44 (d, 3H), 3.67 (s, 3H), 3.91 (q, 1H), 3.95 (s, 3H), 6.89 (d, 1H), 7.45 (d, 1H).

後処理

  1. additionAfter the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 12 hours
  4. customThe reaction mixture was evaporated
  5. additionthe residue was diluted with H2O (6 L)
  6. extractionThe aqueous layer was extracted with CH2Cl2 (15 L)
  7. washThe organic layer was washed with water (10 L) and brine (10 L)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. customThe crude residue was purified by column chromatography (petroleum ether/EtOAc=100:0˜80:20)

出典と根拠

ORDレコード
ord-ad87538bd204462eba0ad26b251570d2
出典データセット
uspto-grants-2016_03
特許番号
US09278953B2

関連ノート

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