Diethyl Malonate → 1,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

HRID 2050791Notes

Reaction equation

HRID 2050791 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Na].[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[O:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([O:17][CH2:18][CH3:19])=[O:16])[CH2:2]1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 135942-Cyclohexen-1-oneHCID 5360545Sodium

Product 1

HCID 3170491,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 30 ml of 2-cyclohexen-1-one in 35 ml anhydrous ethanol is added dropwise at a temperature below -10° to a reagent prepared from 0.1 g sodium, 100 ml of absolute ethanol and 50 ml of diethyl malonate. The reaction mixture is allowed to warm slowly and is stirred at room temperature overnight. The mixture is evaporated to dryness, the residue is dissolved in ether, the ether solution is washed with brine, dried, filtered and evaporated to dryness. The residue is distilled under reduced pressure to yield diethyl 3-oxocyclohexylmalonate, b.p. 147°/0.5 mm.

Workup

  1. temperatureto warm slowly
  2. customThe mixture is evaporated to dryness
  3. dissolutionthe residue is dissolved in ether
  4. washthe ether solution is washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-9075dd9571ef48aabfa56b1fa927b704
Source dataset
uspto-grants-1991_05
Patent number
US05015645

Reaction notes

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