Reaction #685007

Reaction equation

sodium acetate

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

water

ethyl acetate

→

light yellow crystal

Yield 13.6%

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

Yield 13.6%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturethe obtained mixture was then heated
2. 2
   Temperatureto reflux for 5 minutes
3. 3
   TemperatureAfter cooling
4. 4
   Otheran organic layer was separated
5. 5
   WashThe organic layer was successively washed with water
6. 6
   Dryinga 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
    ConcentrationThis reaction mixture was concentrated under a reduced pressure
13. 13
    workup.ADDITIONThereafter, water and ethyl acetate were added
14. 14
    Otheran organic layer was separated
15. 15
    WashThe organic layer was successively washed with water
16. 16
    Dryinga 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
    OtherThe residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1)

Procedure

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.

Source