Ethyl Acetoacetate → Ethyl 2-(4-chlorobenzyl)acetoacetate

HRID 857316Notes

Reaction equation

HRID 857316 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CN(C=O)C>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][CH:4]([C:5](=[O:6])[CH3:7])[C:3]([O:9][CH2:10][CH3:11])=[O:8])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 2757404Ethyl 2-(4-chlorobenzyl)acetoacetateYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (1.6 g, 40 mmol) in DMF (60 mL) at 0° C. was added ethyl acetoacetate (5.7 g, 44 mmol). The mixture was stirred for 30 minutes and p-chlorobenzyl bromide (8.2 g, 40 mmol) was added. The reaction mixture was stirred at r.t. for 2 hours and then quenched with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 10% EtOAc in Hexanes to provide 6.5 g of the title compound as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 2 hours
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 10% EtOAc in Hexanes

Sources & evidence

ORD record
ord-6868f67116934c86987035037a44948e
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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