Water → HCID 58047154, compound

HRID 1888713Notes

Reaction equation

HRID 1888713 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[CH:13]=[C:14]([C:16](=[O:18])[CH3:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[CH:13]=[C:14]([CH:16]([OH:18])[CH3:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 46941687HCID 46941687, compound

Product 1

HCID 58047154HCID 58047154, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[6-(benzyloxy)-1-benzofuran-2-yl]ethanone (25.7 g, 96.6 mmol) in methanol (300 mL) was added sodium borohydride (3.67 g, 96.6 mmol) by small portions, and the mixture was stirred at room temperature for 1 hr. 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 sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to give the title compound (18.3 g, yield 71%).

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 sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-d5db99f5bdb14f0f938131b69443bb4b
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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