1,4-Dioxane → Ethyl 2-nitro-3-(3-nitrophenyl)-5-oxo-5-phenylpentanoate

HRID 1722768Notes

Reaction equation

HRID 1722768 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N+:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])([O-:22])=[O:21].O1CCOCC1>N1CCCCC1.C(O)C>[N+:20]([CH:23]([CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:11][C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 69379Ethyl nitroacetateHCID 948623-Nitrochalcone

Product 1

HCID 10068705Ethyl 2-nitro-3-(3-nitrophenyl)-5-oxo-5-phenylpentanoateYield 19.7%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(3-nitrophenyl)-1-phenyl-2-propen-1-one (0.5 g), ethyl nitroacetate (0.29 g), piperidine (3 drops), dioxane (5 ml) and ethanol (5 ml) was refluxed for 2 hours. After allowing to cooling at ambient temperature, the reaction mixture was evaporated in vacuo. The residue was subjected to a column chromatography on silica gel (50 ml) eluting with benzene. The fractions containing the object compound were combined and concentrated under reduced pressure to give ethyl 2-nitro-3-(3-nitrophenyl)-5-oxo-5-phenylpentanoate (0.15 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. washeluting with benzene
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1986dd0aa9944dcdab0437537a6f5852
Source dataset
uspto-grants-1989_08
Patent number
US04857527

Reaction notes

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