Diethyl Malonate → Propanedioic acid, [(4-methoxyphenyl)methylene]-, diethyl ester

HRID 1859946Notes

Reaction equation

HRID 1859946 reaction equation
N1CCCCC1.[C:7]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].CO[CH2:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(OCC)(=O)C>C(O)C>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:7]([O:15][CH2:16][CH3:17])=[O:14])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 2500744-(Methoxymethoxy)benzaldehyde

Product 1

HCID 81238Propanedioic acid, [(4-methoxyphenyl)methylene]-, diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine (1.5 ml) and diethyl malonate (14.9 ml) were added to a solution of 4-methoxymethoxybenzaldehyde (16.2 g) in ethanol (160 ml). The mixture was heated at reflux for 7 hours. At the end of this time ethyl acetate was added to the reaction mixture and the ethyl acetate was washed with aqueous hydrogen chloride solution (0.8N) and saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=9/1-3/1 as the eluant to afford the desired compound (5.00 g) as a syrup.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 hours
  3. washthe ethyl acetate was washed with aqueous hydrogen chloride solution (0.8N) and saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-fe1561b54ebf47d9b544a4557586efde
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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