Water → HCID 21990154, compound

HRID 597825Notes

Reaction equation

HRID 597825 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][OH:13])[C:8]([O:14][CH3:15])=[CH:7][C:6]=1[OH:16])=O.C([O-])(=O)C.[Na+].O.C(OCC)(=O)C>CO>[CH3:15][O:14][C:8]1[C:9]([CH2:11][CH2:12][OH:13])=[CH:10][C:5]2[CH:3]=[CH:2][O:16][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 21990092HCID 21990092, compound

Product 1

HCID 21990154HCID 21990154, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperaturethe obtained mixture was then heated
  2. temperatureto reflux for 5 minutes
  3. temperatureAfter cooling
  4. customan organic layer was separated
  5. washThe organic layer was successively washed with water
  6. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled away under a reduced pressure
  8. dissolutionThe residue was dissolved in 150 ml of methanol
  9. additionThereafter, 6.30 g of sodium borohydride was dividedly added to the obtained solution
  10. additionSubsequently, 6 mol/l hydrochloric acid was added to the reaction solution, so that the pH
  11. stirringThe obtained solution was further stirred at a room temperature for 1 hour
  12. concentrationThis reaction mixture was concentrated under a reduced pressure
  13. additionThereafter, water and ethyl acetate were added
  14. customan organic layer was separated
  15. washThe organic layer was successively washed with water
  16. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  17. distillationThe solvent was then distilled away under a reduced pressure
  18. customThe residue was purified by column chromatography (eluent:hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5ab2884970f64dbda2b3b279439616b3
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Reaction notes

Loading…