Ethyl Glycolate → Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate

HRID 1360295ノート

反応式

HRID 1360295 の反応式
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[Br:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14](Cl)=[N:15][CH:16]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH2:8]([O:7][C:3](=[O:6])[CH2:4][O:5][C:14]1[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][C:11]([Br:10])=[CH:16][N:15]=1)[CH3:9]

参加物

6

反応物 4

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 70194125-Bromo-2-chloro-3-nitropyridine

生成物 1

HCID 4647502Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate収率 49%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

Sodium hydride (55% dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of ethyl glycolate (1.43 g, 13.8 mmol) in 1,4-dioxane, and the reaction mixture was heated at 70° C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70° C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (Na2SO4), and evaporated. Chromatography (SiO2, hexane-ethyl acetate gradient) furnished (5-bromo-3-nitropyridin-2-yloxy)-acetic acid ethyl ester (1.03 g, 49%). Light yellow liquid, MS (ISP)=305.1 (M+H)+.

後処理

  1. extractionextracted three times with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. customevaporated

出典と根拠

ORDレコード
ord-04254191ba3f4b3795b2169ef2469748
出典データセット
uspto-grants-2011_02
特許番号
US07879845B2

反応ノート

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