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

HRID 1648611

반응식

HRID 1648611 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 34.96 g (0.231 moi) of N-ethyl-3-hydroxybenzylamine in 200 ml of dimethylsulfoxide were added 25.64 g (0.231 mol) of 1,3-dichloropropene (E/Z=2/1) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-88ee3ecf77584c3b9e5fe18705b509f0
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436354

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