تفاعل #685007

معادلة التفاعل

sodium acetate

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

water

ethyl acetate

→

light yellow crystal

المردود 13.6%

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

المردود 13.6%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe obtained mixture was then heated
2. 2
   درجة الحرارةto reflux for 5 minutes
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىan organic layer was separated
5. 5
   غسيلThe organic layer was successively washed with water
6. 6
   تجفيفa 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
    تركيزThis reaction mixture was concentrated under a reduced pressure
13. 13
    workup.ADDITIONThereafter, water and ethyl acetate were added
14. 14
    أخرىan organic layer was separated
15. 15
    غسيلThe organic layer was successively washed with water
16. 16
    تجفيفa 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
    أخرىThe residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1)

الإجراء التجريبي

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.

المصدر