Ethyl Acetoacetate → HCID 10176552, compound

HRID 1699990Notes

Reaction equation

HRID 1699990 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Cl[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16]>CN(C)C=O>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([C:3](=[O:4])[CH3:5])[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH3:9]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 104291-Chloro-3-methyl-2-buteneHCID 24758Sodium hydride

Product 1

HCID 10176552HCID 10176552, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 26.05 g ethyl acetoacetate in 150 ml of dimethylformamide, 8.30 g 60% sodium hydride were added portionwise over 1 hour while the temperature rose to 60° C. After cooling down to room temperature, a solution of 24.8 g 1-chloro-3-methyl-2-butene in 50 ml of dimethylformamide was dropped in. Then the mixture was stirred at room temperature for 2.5 hours. The mixture was quenched with water and extracted with ether. The combined organic phase was dried, filtered and evaporated to dryness. The resulting yellow oil was purified by distillation to yield 23.16 g of a colourless oil.

Workup

  1. customrose to 60° C
  2. customThe mixture was quenched with water
  3. extractionextracted with ether
  4. customThe combined organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. distillationThe resulting yellow oil was purified by distillation

Sources & evidence

ORD record
ord-ad03808fc6114408a3014ea70dc3e323
Source dataset
uspto-grants-2002_02
Patent number
US06348618B1

Reaction notes

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