반응 #684989

반응 방정식

hydrochloric acid

3-azetidinol hydrochloride

potassium carbonate

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

→

achromatic oil

수율 24.5%

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

수율 24.5%

용매

dimethyl sulfoxide

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.WAITat 95° C. for 1.5 hours
2. 2
   온도Thereafter, the reaction solution was cooled
3. 3
   기타a 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
   기타followed by separation of an organic layer
7. 7
   세척The organic layer was successively washed with water
8. 8
   건조a 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
    기타The residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 5:1)

실험 절차

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.

출처