1,4-Dioxane → HCID 86747477, compound

HRID 1197666Notes

Reaction equation

HRID 1197666 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH2:16][C:17](=O)C=C)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:21]/[C:22](/[CH3:33])=[CH:23]\[C:24]([O:26][CH2:27]/[CH:28]=[CH:29]/[CH:30]=[CH:31]/[CH3:32])=[O:25].C(=O)([O-])O.[Na+].O1CCO[CH2:41][CH2:40]1>[Cl-].[Zn+2].[Cl-]>[CH3:33][C:22]1[NH:21][C:40]([CH3:41])=[C:15]([C:14]2[CH:17]=[CH:16][CH:11]=[CH:12][N:13]=2)[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]=1[C:24]([O:26][CH2:27]/[CH:28]=[CH:29]/[CH:30]=[CH:31]/[CH3:32])=[O:25]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 67850751HCID 67850751, compoundHCID 86747478HCID 86747478, compound

Product 1

HCID 86747477HCID 86747477, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

268 mg (1 mmol) of 4-(3-nitrophenyl)-3-pyridyl-3-butene-2-one, 905 mg (5 mmol) of (2E,4E)-2,4-hexadiene-1-yl 3-aminocrotonate, 273 mg (2 mmol) of zinc chloride, and 500 mg of Molecular Shieves 4A were added to 1,4-dioxane. This reaction mixture was refluxed with application of heat in an inert atmoshpere for 5 hours. The reaction mixture was then cooled to room temperature and neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed b extraction with chloroform. The solvents contained in the extract were distilled off and the residue was chromatographed on a silica gel column, whereby the captioned compound was obtained. The yield was 182 mg (42.3%).

Workup

  1. temperatureThis reaction mixture was refluxed with application
  2. temperatureof heat in an inert atmoshpere for 5 hours
  3. extractionb extraction with chloroform
  4. distillationwere distilled off
  5. customthe residue was chromatographed on a silica gel column, whereby the captioned compound
  6. customwas obtained

Sources & evidence

ORD record
ord-3eafa9aa711a4955bd5a1e870a777317
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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