Diethyl Oxalate → Diethyl 2-oxo-3-propylsuccinate

HRID 916641Notes

Reaction equation

HRID 916641 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].[C:10]([O:17][CH2:18][CH3:19])(=[O:16])[C:11]([O:13]CC)=O.CC[O-].[Na+]>CCO>[CH2:18]([O:17][C:10](=[O:16])[C:11](=[O:13])[CH:5]([CH2:6][CH2:7][CH3:8])[C:4]([O:3][CH2:1][CH3:2])=[O:9])[CH3:19]

Participants

5

Reactant 3

HCID 7268Diethyl Oxalate2×HCID 10882Ethyl valerateHCID 2723922Sodium ethoxide

Product 1

HCID 251154Diethyl 2-oxo-3-propylsuccinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, a mixture of pentanoic acid ethyl ester (0.4 mol) and diethyl oxalate (compound 11 in Scheme 1) (73.1 g, 0.5 mol) is added to a solution of NaOEt (32.7 g, 0.48 mol) in EtOH (250 ml). The mixture is stirred at room temperature for 30 minutes and EtOH is distilled away. The residue is then purified by vacuum distillation, which provides the product (120) as a clear oil.

Workup

  1. distillationEtOH is distilled away
  2. distillationThe residue is then purified by vacuum distillation, which

Sources & evidence

ORD record
ord-15ad3ca6cb14451198d03e02caec3108
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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