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

Participants

Reaction Steps

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 2.20 mL of acrylonitrile at 0 to 10° C., which was then stirred at same temperature for 1.5 hours. To this reaction mixture were added 0.1 mL of hydrochloric acid, 10 mL of butanol and 5 mL of 50% (w/w) sulfuric acid, which was then refluxed for 15 hours. After cooling, to the reaction mixture was added 15 mL of water. 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=10:1) to provide 6.65 g of butyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Provenance & Evidence