pentan-3-one O-(2-nitrophenyl)oxime → 2-Ethyl-3-methyl-7-nitrobenzo[b]furan

HRID 342414

Reaction equation

HRID 342414 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10]N=C(CC)CC)([O-:3])=[O:2]>Cl.CO>[CH2:9]([C:4]1[O:10][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]=1[CH3:6])[CH3:8]

Participants

3

Reactant 1

HCID 53768417pentan-3-one O-(2-nitrophenyl)oxime

Product 1

HCID 702012322-Ethyl-3-methyl-7-nitrobenzo[b]furanYield 91.6%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of pentan-3-one O-(2-nitrophenyl)oxime (10.50 g) in 10% hydrogen chloride-methanol (105 ml) was refluxed for 4 hours. After concentration in vacuo, the residue was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated aqueous sodium bicarbonate, brine and dried over, sodium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (eluate; ethyl acetate:n-hexane=1:6) to give a solid. The resulting solid was triturated with a mixture of ethanol and water (2:1) and the precipitate was collected to give 2-ethyl-3-methyl-7-nitrobenzo[b]furan (4.44 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationAfter concentration in vacuo
  3. extractionthe residue was extracted with ethyl acetate and water
  4. washThe obtained organic layer was washed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over, sodium sulfate
  6. customAfter evaporation in vacuo
  7. customthe residue was purified by column chromatography on silica gel (eluate; ethyl acetate:n-hexane=1:6)
  8. customto give a solid
  9. customThe resulting solid was triturated with a mixture of ethanol and water (2:1)
  10. customthe precipitate was collected

Sources & evidence

ORD record
ord-1ff8c5dfd43a4351aebaadb2017d4f8a
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Linked notes

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