Ethyl Acetate → (E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine
Reaktionsgleichung
[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]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
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.
Aufarbeitung
- washwashed with 200 ml ×2 of water and 200 ml of saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- concentrationconcentrated under reduced pressure
- customto obtain 26.2 g (yield: 50%) of the
Quellen und Nachweise
- ORD-Eintrag
- ord-88ee3ecf77584c3b9e5fe18705b509f0
- Quelldatensatz
- uspto-grants-1995_07
- Patentnummer
- US05436354
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