Ethyl Acetoacetate → HCID 59487381, compound

HRID 1099585Notes

Reaction equation

HRID 1099585 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.C[C:11]1([CH3:19])[O:16]C(=O)CC(=O)O1.[C:20]([O-])(=O)[CH3:21].[NH4+:24].[CH3:25][CH:26]([CH3:30])CC=O>C(O)(=O)C>[CH2:5]([CH:3]1[CH2:19][C:11](=[O:16])[NH:24][C:20]([CH3:21])=[C:2]1[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:26]([CH3:30])[CH3:25]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 115523-MethylbutanalHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium Acetate

Product 1

HCID 59487381HCID 59487381, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

6.13 g (47.1 mmol) of ethyl acetoacetate, 6.79 g (47.1 mmol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 3.99 g (51.8 mmol) of ammonium acetate were initially charged in 50 ml of acetic acid, and 5.053 ml (47.1 mmol) of 3-methylbutyraldehyde were added. The mixture was then stirred at an oil bath temperature of 130° C. overnight. After removal of the volatile components on a rotary evaporator, the residue was taken up in 100 ml of ethyl acetate and 100 ml of water were added. The aqueous phase was extracted with ethyl acetate. The combined organic phases were then washed with aqueous 2M sodium carbonate solution and then with concentrated aqueous sodium chloride solution. After drying with magnesium sulfate, the solvent was removed on a rotary evaporator. The crude product was taken up in 25 ml of diisopropyl ether and dissolved in the hot solvent. Crystallisation was then initiated with 3 ml of n-pentane. The precipitated solid was isolated by filtration and then washed with 2 ml of diisopropyl ether. Drying under high vacuum gave 1.40 g (12% of theory) of the target compound.

Workup

  1. customAfter removal of the volatile components
  2. customon a rotary evaporator
  3. addition100 ml of water were added
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic phases were then washed with aqueous 2M sodium carbonate solution
  6. dry with materialAfter drying with magnesium sulfate
  7. customthe solvent was removed on a rotary evaporator
  8. dissolutiondissolved in the hot solvent
  9. customCrystallisation
  10. customThe precipitated solid was isolated by filtration
  11. washwashed with 2 ml of diisopropyl ether
  12. customDrying under high vacuum
  13. customgave 1.40 g (12% of theory) of the target compound

Sources & evidence

ORD record
ord-64cff31a99f0456ca556cefb8083ed94
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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