Ethyl Acetoacetate → HCID 21877113, compound

HRID 723617Notes

Reaction equation

HRID 723617 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:10])[CH2:6][C:7]([CH3:9])=[O:8])[CH3:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:15]Cl>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:15][CH:6]([C:7](=[O:8])[CH3:9])[C:5]([O:4][CH2:2][CH3:3])=[O:10]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 1378803,5-Dichlorobenzyl chlorideHCID 5360545Sodium

Product 1

HCID 21877113HCID 21877113, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (1.01 g, 44 mmol) was added to ethanol (100 ml) and stirred until all the metal had dissolved. Ethylacetoacetate (15.6 g, 111 mmol) was added and the reaction mixture was stirred under a nitrogen atmosphere for 10 minutes. 3,5-dichlorobenzyl chloride (7.24 g, 40 mmol) was added and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was filtered and the solution was concentrated under reduced pressure. The orange oil was purified by flash chromatography on silica gel eluting with pentane followed by pentane:ethyl acetate (30:1, by volume) to afford the title compound as a colourless oil (6.4 g).

Workup

  1. dissolutionhad dissolved
  2. stirringthe reaction mixture was stirred under a nitrogen atmosphere for 10 minutes
  3. stirringthe reaction mixture was stirred at room temperature for 3 days
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe solution was concentrated under reduced pressure
  6. customThe orange oil was purified by flash chromatography on silica gel eluting with pentane

Sources & evidence

ORD record
ord-0eed8688323e447eab95509d5232ae12
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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