2,2-Diethoxyethanol → 4-(2,2-Diethoxyethoxy)-3-methoxyaniline

HRID 1181337

反応式

HRID 1181337 の反応式
[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]

参加物

5

反応物 3

HCID 121292,2-DiethoxyethanolHCID 24758Sodium hydrideHCID 705192-Chloro-5-nitroanisole

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fa3def94d51e47a4b2dc6b59b433afbe
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

関連ノート

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