反応 #684996

反応方程式

water

acetone

2-(2-(1-benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone

hydrochloric acid

→

yellow oil

1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol

溶媒

tetrahydrofuran

ethyl acetate

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise to the obtained solution
2. 2
   温度while cooling on ice
3. 3
   workup.STIRRINGthe obtained mixture was then stirred for 30 minutes
4. 4
   温度the obtained mixture was heated
5. 5
   温度to reflux for 2 hours
6. 6
   温度After the reaction mixture was cooled
7. 7
   その他a water layer was separated
8. 8
   workup.ADDITIONThereafter, ethyl acetate was added to the water layer
9. 9
   workup.ADDITIONThe pH of the obtained mixture was adjusted to pH 9.5 by addition of a 2 mol/l aqueous sodium hydroxide solution
10. 10
    その他followed by separation of an organic layer
11. 11
    洗浄The organic layer was successively washed with water
12. 12
    乾燥a saturated saline solution, and then dried over anhydrous magnesium sulfate
13. 13
    workup.DISTILLATIONThereafter, the solvent was distilled away under a reduced pressure
14. 14
    その他The residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 20:1)

実験手順

The above 2-(2-(1-benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone was dissolved in 7.4 ml of tetrahydrofuran. Thereafter, 7.4 ml of a tetrahydrofuran solution containing a 1 mol/l borane-tetrahydrofuran complex was added dropwise to the obtained solution while cooling on ice, and the obtained mixture was then stirred at a room temperature for 17 hours. Thereafter, 10 ml of acetone was added to the reaction mixture, and the obtained mixture was then stirred for 30 minutes. Thereafter, 1.5 ml of 6 mol/l hydrochloric acid was added thereto, and the obtained mixture was heated to reflux for 2 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and a water layer was separated. Thereafter, ethyl acetate was added to the water layer. The pH of the obtained mixture was adjusted to pH 9.5 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 20:1), so as to obtain 0.53 g of a yellow oil product, 1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol.

出典