Hydrochloric Acid → Propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence