Sodium ethoxide → HCID 68581585, compound

HRID 1435603Notes

Reaction equation

HRID 1435603 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]([N:8]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:9][CH2:10][C:11]([O:13]CC)=O)=[O:7])[CH3:2].[O-]CC.[Na+]>C(O)C>[CH:16]1([N:8]2[CH2:9][CH2:10][C:11](=[O:13])[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:22])[C:6]2=[O:7])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 68581951HCID 68581951, compound

Product 1

HCID 68581585HCID 68581585, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Cyclohexyl-N-(2-ethoxycarbonyl-ethyl)-malonamic acid ethyl ester (5.40 g, 17.2 mmol) was heated with sodium ethoxide (2.34 g, 3.44 mmol) in refluxing ethanol (100 ml) for 3 hours. The cooled solution was concentrated, water (100 ml) was added and the solution washed with ether then isohexane. It was acidified with c. sulphuric acid to pH 2. The oily precipitate was extracted into dichloromethane, wahed with brine, dried (MgSO4) and concentrated to a yellow oil weighing 3.6 g (67%).

Workup

  1. concentrationThe cooled solution was concentrated
  2. additionwater (100 ml) was added
  3. washthe solution washed with ether
  4. extractionThe oily precipitate was extracted into dichloromethane
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-9e0dc008912f4b69be949a92c6a7f88a
Source dataset
uspto-grants-2009_11
Patent number
US07618966B2

Reaction notes

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