Diethyl Malonate → HCID 69640128, compound

HRID 1241542Notes

Reaction equation

HRID 1241542 reaction equation
[O-][CH2:2][CH3:3].[Na+].C(O[C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C.C(O[C:19](=[O:33])[C:20](=[C:30]([NH2:32])[CH3:31])[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C>C(O)C>[CH2:13]([O:12][C:10]([C:9]1[C:8](=[O:15])[N:32]([CH2:2][CH3:3])[C:30]([CH3:31])=[C:20]([CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]=1[OH:33])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 69640137HCID 69640137, compound

Product 1

HCID 69640128HCID 69640128, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide in ethanol (27.5 ml; 0.0738 mol) was stirred and refluxed. Malonic acid diethyl ester (11.8 ml; 0.0738 mol) was added dropwise. A solution of intermediate 23 (8.3 g; 0.0335 mol) in ethanol (30 ml) was added dropwise. The mixture was stirred and refluxed for 15 hours. Three-quarters of EtOH were evaporated. The mixture was poured out in ice, acidified with HCl 3N and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated The residue (19.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/NH4OH 96/4/0.1; 15–35 μm). Two fractions were collected and the solvent was evaporated and dried to yield 0.43 g (4%).

Workup

  1. temperaturerefluxed
  2. temperaturerefluxed for 15 hours
  3. customThree-quarters of EtOH were evaporated
  4. additionThe mixture was poured out in ice
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated The residue (19.5 g)
  10. customwas purified by column chromatography over silica gel (eluent: CH2Cl2/NH4OH 96/4/0.1; 15–35 μm)
  11. customTwo fractions were collected
  12. customthe solvent was evaporated
  13. customdried
  14. customto yield 0.43 g (4%)

Sources & evidence

ORD record
ord-66dc517642ad4edb837ee61a5d334a9b
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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