Water → 1-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanol

HRID 1888742Notes

Reaction equation

HRID 1888742 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([C:18](=[O:20])[CH3:19])=[CH:15][C:14]=3[CH:21]=2)=[CH:6][CH:5]=1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([OH:20])[CH3:19])=[CH:15][C:14]=3[CH:21]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 670158661-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone

Product 1

HCID 580474551-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanolYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the obtained 1-{5-[(4-ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone (6.95 g) in methanol (50 mL) was added sodium borohydride (1.04 g, 27.4 mmol) by small portions, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture, and the solvent was evaporated. Ethyl acetate was added thereto, and the mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=3:2) to give the title compound (2.87 g, yield 67%).

Workup

  1. customthe solvent was evaporated
  2. additionEthyl acetate was added
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-fb94cc59b4bc4e1ab3c715f2c99a6bb8
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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