反応 #7534

反応方程式

hydrochloric acid

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

3-azetidinol hydrochloride

potassium carbonate

→

1-{3-[2-(1-benzothiophen-6-yl)ethoxy]propyl}-3-azetidinol

収率 24.5%

溶媒

dimethyl sulfoxide

ethyl acetate

water

反応条件

後処理

1. 1
   workup.ADDITIONwere added to the solution
2. 2
   workup.WAITat 95° C. for 1.5 hours
3. 3
   温度After the reaction mixture was cooled
4. 4
   その他the aqueous layer was separated
5. 5
   workup.ADDITIONEthyl acetate was added to the aqueous layer
6. 6
   その他after which the organic layer was separated
7. 7
   洗浄The organic layer was washed with water
8. 8
   乾燥a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONdistilled under reduced pressure
10. 10
    その他to remove the solvent
11. 11
    その他The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1)

実験手順

In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 6-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the solution. The resulting mixture was stirred at 75° C. for 2.5 hours and then at 95° C. for 1.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer and the. pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1) to obtain 0.28 g of 1-{3-[2-(1-benzothiophen-6-yl)ethoxy]propyl}-3-azetidinol as a colorless oil.

出典