Acetamidomalonic acid diethyl ester → HCID 54344374, compound

HRID 1451573Notes

Reaction equation

HRID 1451573 reaction equation
[CH2:1](Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([NH:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12].[O-]CC.[Na+]>C(O)C>[C:11]([NH:14][C:15]([CH2:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 98116BromomethylstyreneHCID 2723922Sodium ethoxide

Product 1

HCID 54344374HCID 54344374, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.42 g of cinnamyl bromide, 5.43 g of diethyl 2-acetamidomalonate and 1.87 g of sodium ethoxide in 70 ml of ethanol was refluxed under heating for 2 hours under a nitrogen atmosphere. The mixture was poured into 200 ml of ice water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:3) to give 2.68 g of diethyl 2-acetamido-2-(3-phenyl-2-propenyl)malonate as white crystals.

Workup

  1. temperatureunder heating for 2 hours under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:3)

Sources & evidence

ORD record
ord-1e730ebfd7ec4464b3b7fea3727c4f25
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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