Diethyl Malonate → HCID 69655184, compound

HRID 1241874Notes

Reaction equation

HRID 1241874 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].CS(O[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])(=O)=O>CCO>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 21887967HCID 21887967, compound

Product 1

HCID 69655184HCID 69655184, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.9 mL (0.223 mol) of diethyl malonate were added, under a nitrogen atmosphere and at room temperature, to a solution of sodium ethoxide (prepared in situ by dissolving 2.6 g (0.0151 mol) of Na in 80 mL of absolute EtOH). After 30 min, 14.5 g (0.0677 mol) of 2-methylphenethyl alcohol methanesulphonate dissolved in 40 mL of abs. EtOH were added dropwise and the resulting solution was heated to reflux for 3 h. EtOH was removed in vacuo, the residue was taken up in water and extracted with Et2O. The organic phase was washed successively with 10% HCl and brine, dried and the solvent was removed in vacuo. The excess diethyl malonate was removed by distillation under reduced pressure. The resulting oil (15.6 g) was used without further purification.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 3 h
  3. customEtOH was removed in vacuo
  4. extractionextracted with Et2O
  5. washThe organic phase was washed successively with 10% HCl and brine
  6. customdried
  7. customthe solvent was removed in vacuo
  8. customThe excess diethyl malonate was removed by distillation under reduced pressure
  9. customThe resulting oil (15.6 g) was used without further purification

Sources & evidence

ORD record
ord-8a2af135e22b4f328d3cb9e1f4548afa
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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