Reaktion #640403

Reaktionsgleichung

benzyltrimethylammonium hydroxide

acrylonitrile

hydrochloric acid

methanol

hydrogen chloride

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

→

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

Lösungsmittel

toluene

water

tetrahydrofuran

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas then refluxed for 4 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 5.00 g of 2-(1-benzothiophen-5-yl)ethanol were added 0.23 g of 40% (w/w) benzyltrimethylammonium hydroxide aqueous solution and 2.28 mL of tetrahydrofuran, and dropwise added 2.22 mL of acrylonitrile at 5° C., which was then stirred at 0 to 15° C. for 1.5 hours. To this reaction mixture were added 0.13 mL of hydrochloric acid, 10 mL of methanol and 1.52 g of water. Thereto was introduced 9.47 g of hydrogen chloride, which was then refluxed for 4 hours. After cooling, to the reaction mixture were added 15 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=5:1) to provide 7.36 g of methyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Quelle