2,2-二乙氧基乙醇 → 4-(2,2-Diethoxyethoxy)-3-methoxyaniline

HRID 1181337

反应方程式

HRID 1181337 反应方程式
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][OH:6])[CH3:2].[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[O:22][CH3:23]>CN(C=O)C>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][O:6][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[O:22][CH3:23])[CH3:2]

参与物

5

反应物 3

HCID 121292,2-二乙氧基乙醇HCID 24758氢化钠HCID 705192-氯-5-硝基茴香醚

产物 1

HCID 114367644-(2,2-Diethoxyethoxy)-3-methoxyaniline

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a solution of 2,2-diethoxyethanol (50 mmol, 6.71 g) was added 60% sodium hydride (50 mmol, 2.0 g) and the solution was stirred for 10 minutes at which point a solution of 2-chloro-5-nitroanisole (50 mmol, 9.38 g ) in DMF was added dropwise. The reaction mixture was stirred for 18 h. The DMF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated. The principal component was purified by silica gel column chromatography. The product was subjected to reduction over 18 h using 1 atm hydrogen and 10% Pd on carbon. After the reaction took up a theoretical amount of hydrogen the catalyst was removed by filtration.

后处理

  1. additionwas added dropwise
  2. customThe DMF was removed by rotary evaporation
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe principal component was purified by silica gel column chromatography
  8. waitThe product was subjected to reduction over 18 h
  9. customwas removed by filtration

来源与证据

ORD记录
ord-fa3def94d51e47a4b2dc6b59b433afbe
来源数据集
uspto-grants-2007_10
专利号
US07285557B2

关联笔记

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