Diethyl Oxalate → HCID 66958840, compound

HRID 1360436Notes

Reaction equation

HRID 1360436 reaction equation
CC(C)([O-])C.[Na+].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8]([O:10]CC)=O.[C:17]1(=[O:32])[N:21]([CH2:22][CH2:23][C:24](=[O:26])[CH3:25])[C:20](=[O:27])[C:19]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:18]12.[Na]>C(O)C>[O:10]=[C:8]([CH2:25][C:24](=[O:26])[CH2:23][CH2:22][N:21]1[C:17](=[O:32])[C:18]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:19]2[C:20]1=[O:27])[C:7]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 5360545SodiumHCID 23676156Sodium t-butoxide

Product 1

HCID 66958840HCID 66958840, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Phthalimido-2-butanone was obtained from the literature procedure, Eriks et al, J. Med. Chem., 1992, 35, 3239-3246. Sodium tert-butoxide (20.75 g, 0.216 mol) was added over a period of 12 minutes to ethanol (160 mL) under a nitrogen atmosphere. When all solids had dissolved, diethyl oxalate (31.55 g, 0.216 mol) and a suspension of 4-phthalimido-2-butanone (46.9 g, 0.216 mol) were sequentially added. The reaction was stirred at ambient temperature for 2.5 hours. A precipitate was present and was isolated by filtration to provide 37.4 g of ethyl 2,4-dioxo-6-phthalimidohexanoate, sodium salt as a light orange solid.

Workup

  1. dissolutionWhen all solids had dissolved
  2. additionwere sequentially added
  3. customwas isolated by filtration

Sources & evidence

ORD record
ord-4b87854bbbde4c30a150f70dc43d6ac1
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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