Tetrahydrofuran → HCID 86748896, compound

HRID 1756813Notes

Reaction equation

HRID 1756813 reaction equation
C(=NO)([NH2:3])C.[H-].[Na+].[C:8](OCC)(=O)/[CH:9]=[CH:10]/[CH:11]=C/C.[Cl-].[NH4+:19].[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:21][C:22]([C:23]1[N:19]=[N:3][O:20][CH:24]=1)=[CH:8][CH:9]=[CH:10][CH3:11]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 30926N-HydroxyacetamidineHCID 1550470Ethyl sorbate

Product 1

HCID 86748896HCID 86748896, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetamidoxime (640 mg, 8.64 mmol) was dissolved in tetrahydrofuran (10 ml), 60% sodium hydride (345 mg, 8.63 mmol) was added thereto, 10 particles of molecular sieve and ethyl sorbate (1.1 g, 7.85 mmol) were added thereto, and the mixture was stirred under heating at reflux for 8 hours. The reaction mixture was diluted with ethyl acetate, and an aqueous saturated solution of ammonium chloride was added thereto to stop the reaction. The ethyl acetate layer was separated, washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1-10:1-5:1) to obtain methyloxadiazolyl-1,3-pentadiene (546 mg, 46.3%) as white solid. This compound has the following NMR spectrum.

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 8 hours
  3. customthe reaction
  4. customThe ethyl acetate layer was separated
  5. washwashed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1-10:1-5:1)

Sources & evidence

ORD record
ord-3138420d1cbc4f96b212fa5ba6444a86
Source dataset
uspto-grants-1995_08
Patent number
US05442062

Reaction notes

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