Hydrochloric Acid → 1-(3-(2-(1-Benzothiophene-3-yl)ethoxy)propyl)-3-azetidinol

Participants

Reaction Conditions

Reaction Steps

1.00 g of 3-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 5 ml of dimethyl sulfoxide. Thereafter, 1.10 g of 3-azetidinol trifluoroacetate and 1.63 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 70° C. for 2 hours. After cooling, water and ethyl acetate were added to the reaction mixture. The pH of the mixture was adjusted to pH 1 by addition of 6 mol/l hydrochloric acid, and a water layer was then separated. Ethyl acetate was added to the water layer, and the pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution, followed by separation of an organic layer. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1), so as to obtain 0.55 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-3-yl)ethoxy)propyl)-3-azetidinol.

Provenance & Evidence