Reaktion #685007

Reaktionsgleichung

sodium acetate

2-bromo-1-(2-hydroxy-5-(2-hydroxyethyl)-4-methoxyphenyl)-1-ethanone

water

ethyl acetate

→

light yellow crystal

Ausbeute 13.6%

2-(6-methoxy-1-benzofuran-5-yl)-1-ethanol

Ausbeute 13.6%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe obtained mixture was then heated
2. 2
   Temperaturto reflux for 5 minutes
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigean organic layer was separated
5. 5
   WaschenThe organic layer was successively washed with water
6. 6
   Trocknena saturated saline solution, and then dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was then distilled away under a reduced pressure
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 150 ml of methanol
9. 9
   workup.ADDITIONThereafter, 6.30 g of sodium borohydride was dividedly added to the obtained solution
10. 10
    workup.ADDITIONSubsequently, 6 mol/l hydrochloric acid was added to the reaction solution, so that the pH
11. 11
    workup.STIRRINGThe obtained solution was further stirred at a room temperature for 1 hour
12. 12
    EinengenThis reaction mixture was concentrated under a reduced pressure
13. 13
    workup.ADDITIONThereafter, water and ethyl acetate were added
14. 14
    Sonstigean organic layer was separated
15. 15
    WaschenThe organic layer was successively washed with water
16. 16
    Trocknena saturated saline solution, and then dried over anhydrous magnesium sulfate
17. 17
    workup.DISTILLATIONThe solvent was then distilled away under a reduced pressure
18. 18
    SonstigeThe residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1)

Vorschrift

16.4 g of the above 2-bromo-1-(2-hydroxy-5-(2-hydroxyethyl)-4-methoxyphenyl)-1-ethanone was dissolved in 70 ml of methanol. Thereafter, 17.3 g of sodium acetate was added to the obtained solution, and the obtained mixture was then heated to reflux for 5 minutes. After cooling, water and ethyl acetate were added to the reaction mixture, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The solvent was then distilled away under a reduced pressure. The residue was dissolved in 150 ml of methanol. Thereafter, 6.30 g of sodium borohydride was dividedly added to the obtained solution, and the obtained mixture was stirred at a room temperature for 1 hour. Subsequently, 6 mol/l hydrochloric acid was added to the reaction solution, so that the pH thereof was adjusted to pH 1. The obtained solution was further stirred at a room temperature for 1 hour. This reaction mixture was concentrated under a reduced pressure. Thereafter, water and ethyl acetate were added thereto, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The solvent was then distilled away under a reduced pressure. The residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1), so as to obtain 1.48 g of a light yellow crystal, 2-(6-methoxy-1-benzofuran-5-yl)-1-ethanol.

Quelle