Diethyl Malonate → HCID 4739197, compound

HRID 1973503Notes

Reaction equation

HRID 1973503 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9]CC)=O.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[CH:22][C:23](=[O:25])[CH3:24]>>[O:9]=[C:7]1[CH2:24][C:23](=[O:25])[CH2:22][CH:21]([C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)[CH:6]1[C:5]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 212930Furfural acetoneHCID 2723922Sodium ethoxide

Product 1

HCID 4739197HCID 4739197, compound

Procedure

To a solution of sodium ethoxide (from 2.3 g. sodium and dry ethanol 35 ml.) was added slowly diethyl malonate (14 g.). After the addition the mixture was heated under reflux for 1 minute, cooled and then treated with 4-(2-furyl)-3-buten -2-one (13 g.). After heating under reflux for 17 hrs. and cooling, the precipitated sodium enolate salt (of formula III) was collected by filtration, washed with acetone and dissolved in water. The solution was acidified with 2N-sulphuric acid (to convert the enolate salt to the corresponding dione II) and extracted with dichloromethane. After washing the organic layer with water and drying over sodium sulphate, removal of solvents under reduced pressure afforded ethyl 2,4-dioxo-6-(2-furyl)-cyclohexanecarboxylate.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 1 minute
  4. temperaturecooled
  5. temperatureAfter heating
  6. temperatureunder reflux for 17 hrs
  7. temperatureand cooling
  8. filtrationthe precipitated sodium enolate salt (of formula III) was collected by filtration
  9. washwashed with acetone
  10. dissolutiondissolved in water
  11. extractionextracted with dichloromethane
  12. washAfter washing the organic layer with water
  13. dry with materialdrying over sodium sulphate, removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-dfb325ed2a3049ddb8be487d11cfa7c9
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

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