反応 #7536

反応方程式

hydrochloric acid

5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene

3-azetidinol hydrochloride

sodium hydroxide

→

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol

収率 64.2%

溶媒

dimethyl sulfoxide

ethyl acetate

water

反応条件

後処理

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

実験手順

In 30 mL of dimethyl sulfoxide was dissolved 6.50 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and to the solution were added 5.60 g of 3-azetidinol hydrochloride and 15.3 mL of a 5.mol/L aqueous sodium hydroxide solution, after which the resulting mixture was stirred at 65° C. for 3.5 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 5 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 10:1) to obtain 4.77 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol.

出典