(E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide → N-[2-(5-Methoxy-1H-inden-3-yl)ethyl]acetamide

HRID 582210Notes

Reaction equation

HRID 582210 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH:14][C:15](=[O:17])[CH3:16])=[CH:5][CH:4]=1>FC(F)(F)C(O)=O.O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[CH2:7][CH:8]=[C:9]2[CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

5

Reactant 1

HCID 59957023(E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide

Product 1

HCID 54016815N-[2-(5-Methoxy-1H-inden-3-yl)ethyl]acetamideYield 90.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The (E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]-acetamide (1.0 g, 4.32 mmol) thus obtained was dissolved in trifluoroacetic acid(6 ml)-tetrahydrofuran(6 ml) and the solution was refluxed for 1.5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol=96:4) to provide the title compound (yield 0.9 g, 90%).

Workup

  1. temperaturethe solution was refluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed serially with saturated saline and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol=96:4)

Sources & evidence

ORD record
ord-4565cd77d32543e7903de635a35c357a
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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