Water → 1-(Benzofuran-5-yl)ethanone

HRID 1038600Notes

Reaction equation

HRID 1038600 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)C.O>C1(C)C=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=2[CH:4]=[CH:5]1

Participants

4

Reactant 2

HCID 962WaterHCID 636297741-(4-(2,2-Diethoxyethoxy)phenyl)ethanone

Product 1

HCID 186937521-(Benzofuran-5-yl)ethanoneYield 3.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(4-(2,2-diethoxyethoxy)phenyl)ethanone (2.46 g, 7.34 mmol) in toluene (25 mL), was added PPA (2.50 g) and refluxed for 1 hour. Under ice-cold conditions, the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (44 mg (yield 3.7%)) was obtained as a white solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-45e55d23ac7c4ba6a904f03e879d7a20
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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