Diethyl methylmalonate → HCID 13119616, compound

HRID 1005691Notes

Reaction equation

HRID 1005691 reaction equation
[Na].[CH3:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Cl)([O-:16])=[O:15].[Cl-].[NH4+]>C(O)C>[CH3:2][C:3]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1)([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 11857Diethyl methylmalonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 25517Ammonium ChlorideHCID 5360545Sodium

Product 1

HCID 13119616HCID 13119616, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (45 ml) was dissolved sodium (0.7 g), and diethyl methylmalonate (5.26 ml) and 3-nitrobenzyl chloride (5 g) were added thereto, followed by heating under reflux for 2 hours. The reaction mixture was ice-cooled, an aqueous saturated ammonium chloride was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (9.724 g) as a pale yellow oil.

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. extractionby extracting with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-00f6c71bb57c46c1bf3c1693edd6306d
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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