Sodium ethoxide → HCID 68581585, compound

HRID 1966015Notes

Reaction equation

HRID 1966015 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-ce9da723f0fc464b870a8c5552fff783
Source dataset
uspto-grants-2013_04
Patent number
US08420637B2

Reaction notes

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