Reaktion #640399

Reaktionsgleichung

hydrochloric acid

sulfuric acid

water

2-(1-benzothiophen-5-yl)ethanol

acrylonitrile

water

benzyltrimethylammonium hydroxide

→

propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Lösungsmittel

propanol

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas then refluxed for 6.5 hours
2. 2
   TemperaturAfter cooling, to the reaction mixture
3. 3
   SonstigeThe organic layer was separated
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   FiltrationAfter insoluble matter was filtered off
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   SonstigeThe resultant residue was purified

Vorschrift

To toluene (5 mL) suspension of 0.23 g of 40% (w/w) benzyltrimethylammonium hydroxide aqueous solution was added 5.00 g of 2-(1-benzothiophen-5-yl)ethanol, and dropwise added 2.20 mL of acrylonitrile at 0 to 5° C., which was then stirred at 0 to 20° C. for 1 hour. To this reaction mixture was added 0.125 mL of hydrochloric acid. Thereto were added 10 mL of propanol, 1.0 mL of water and 3.1 mL of sulfuric acid, which was then refluxed for 6.5 hours. After cooling, to the reaction mixture were added 10 mL of water and 10 mL of toluene. The organic layer was separated, and dried over anhydrous magnesium sulfate. After insoluble matter was filtered off, the solvent was distilled off under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=15:1 to 7:1) to provide 7.21 g of propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Quelle