Reacción #684989

Ecuación de reacción

hydrochloric acid

3-azetidinol hydrochloride

potassium carbonate

6-(2-(3-chloropropoxy)ethyl)-1-benzothiophene

→

achromatic oil

Rendimiento 24.5%

1-(3-(2-(1-benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol

Rendimiento 24.5%

Disolventes

dimethyl sulfoxide

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat 95° C. for 1.5 hours
2. 2
   TemperaturaThereafter, the reaction solution was cooled
3. 3
   Otroa water layer was then separated
4. 4
   workup.ADDITIONEthyl acetate was added to the water layer
5. 5
   workup.ADDITIONthe pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution
6. 6
   Otrofollowed by separation of an organic layer
7. 7
   LavadoThe organic layer was successively washed with water
8. 8
   Secadoa saturated saline solution, and then dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThereafter, the solvent was distilled away under a reduced pressure
10. 10
    OtroThe residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 5:1)

Procedimiento

1.00 g of 6-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 5 ml of dimethyl sulfoxide. Thereafter, 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the obtained solution, and the obtained mixture was stirred at 75° C. for 2.5 hours, and then at 95° C. for 1.5 hours. Thereafter, the reaction solution was cooled, and thereafter, water and ethyl acetate were added to the reaction mixture. The pH of the obtained 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 5:1), so as to obtain 0.28 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol.

Fuente