Acetamidomalonic acid diethyl ester → Diethyl 2-acetamido-2-pentenylmalonate

HRID 617856Notes

Reaction equation

HRID 617856 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].Br[CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]>C(O)C>[C:1]([NH:4][C:5]([CH:21]=[CH:22][CH2:23][CH2:24][CH3:25])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 707041-Pentene, 5-bromo-HCID 2723922Sodium ethoxide

Product 1

HCID 57066425Diethyl 2-acetamido-2-pentenylmalonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl acetamidomalonate (6.0 g) was dissolved in 50 ml of dehydrated ethanol and 2.26 g of sodium ethoxide and 5.22 g of 5-bromo-1-pentene were added thereto. The mixture was refluxed under a nitrogen atmosphere overnight. The reaction mixture was neutralized and concentrated. The concentrate was purified by silica gel column chromatography using hexane-ethyl acetate (5:1→2:1) as an eluent to give 4.871 g of colorless, oily diethyl 2-acetamido-2-pentenylmalonate.

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere overnight
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-401ff00e4250457d8e5b83b6f164e822
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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