Ethyl Acetoacetate → HCID 10879985, compound

HRID 1795446Notes

Reaction equation

HRID 1795446 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br)([O-:14])=[O:13].[NH4+].[Cl-]>C1COCC1>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][CH:4]([C:5]([CH3:7])=[O:6])[C:3]([O:9][CH2:10][CH3:11])=[O:8])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 10879985HCID 10879985, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (1.94 g, 60%) is added to the solution of ethyl acetoacetate (6.02 g) in THF (100 ml) at 0° C. under nitrogen atmosphere. The reaction mixture is stirred for 15 minutes at the temperature and 3-nitrobenzylbromide (10 g) is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is poured into saturated NH4Cl aq. and extracted with EtOAc twice. The combined organic extract is washed with brine and dried over MgSO4. Concentration under reduced pressure gives the residue which is purified over column chromatography to afford ethyl 2-(3-nitrobenzyl)-acetoacetate (12 g).

Workup

  1. additionis added
  2. extractionextracted with EtOAc twice
  3. extractionThe combined organic extract
  4. washis washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationConcentration under reduced pressure
  7. customgives the residue which
  8. customis purified over column chromatography

Sources & evidence

ORD record
ord-22825c76586b46b891f48791ef48048b
Source dataset
uspto-grants-2006_04
Patent number
US07026491B2

Reaction notes

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