반응 #685007

반응 방정식

sodium acetate

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

water

ethyl acetate

→

light yellow crystal

수율 13.6%

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

수율 13.6%

용매

methanol

반응 조건

후처리

1. 1
   온도the obtained mixture was then heated
2. 2
   온도to reflux for 5 minutes
3. 3
   온도After cooling
4. 4
   기타an organic layer was separated
5. 5
   세척The organic layer was successively washed with water
6. 6
   건조a 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
    농축This reaction mixture was concentrated under a reduced pressure
13. 13
    workup.ADDITIONThereafter, water and ethyl acetate were added
14. 14
    기타an organic layer was separated
15. 15
    세척The organic layer was successively washed with water
16. 16
    건조a 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
    기타The residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1)

실험 절차

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.

출처