Dimethyl 3-oxoglutarate → 2-(1,2-Dimethoxy-ethylidene)-3-oxo-pentanedioic acid dimethyl ester

HRID 1724848Notes

Reaction equation

HRID 1724848 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[O:4].[CH3:13][O:14][C:15](OC)(OC)[CH2:16][O:17][CH3:18]>C(OC(=O)C)(=O)C>[CH3:12][O:11][C:9](=[O:10])[C:8](=[C:16]([O:17][CH3:18])[CH2:15][O:14][CH3:13])[C:6](=[O:7])[CH2:5][C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 74591Dimethyl 3-oxoglutarateHCID 1418971,1,1,2-Tetramethoxyethane

Product 1

HCID 765662492-(1,2-Dimethoxy-ethylidene)-3-oxo-pentanedioic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Dimethyl 1,3-acetonedicarboxylate (20.0 g, 115 mmol) is dissolved in a solution of 1,1,1,2-tetramethoxy-ethane (23.8 g, 158 mmol) and acetic anhydride (420 mL) and the solution is heated to reflux for 4 hours. The mixture is concentrated under reduced pressure. Toluene (200 mL) is added and the solvent removed under reduced pressure to yield the title compound.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. additionToluene (200 mL) is added
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-048cf0f5213b4d73b8a33e9476c45274
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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