Ethyl Acetate → (E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine

HRID 484531ノート

反応式

HRID 484531 の反応式
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:2].[Cl:12][CH:13]=[CH:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[Cl:12]/[CH:13]=[CH:14]/[CH2:15][N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH2:1][CH3:2]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 248831,3-DichloropropeneHCID 100576883-((Ethylamino)methyl)phenol

生成物 1

HCID 10376384(E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine収率 50%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 34.96 g (0.231 mol) of N-ethyl-3-hydroxybenzylamine in 200 ml of dimethylsulfoxide were added 25.64 g (0.231 mol) of 1,3-dichloropropene (E/Z=1) and 16.7 g (0.121 mol) of ground potassium carbonate under ice cooling. The mixture was stirred for 4 hours at 50° C., poured into 250 ml of ethyl acetate, washed with 200 ml×2 of water and 200 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 26.2 g (yield: 50%) of the above identified compound as an oil.

後処理

  1. washwashed with 200 ml×2 of water and 200 ml of saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. customto obtain 26.2 g (yield: 50%) of the

出典と根拠

ORDレコード
ord-bcd3340272fa466ea8455d817aa593cb
出典データセット
uspto-grants-1993_07
特許番号
US05231183

反応ノート

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