Ethyl isobutyrylacetate → HCID 69107640, compound

HRID 2224657Notes

Reaction equation

HRID 2224657 reaction equation
CC[O-].[Na+].[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH:6]([CH3:8])[CH3:7].ClO[N:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1>CCO>[CH2:14]([O:13][C:11]([C:10]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[N:18][O:9][C:5]=1[CH:6]([CH3:8])[CH3:7])=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 81583Ethyl isobutyrylacetateHCID 2723922Sodium ethoxideHCID 86611817HCID 86611817, compound

Product 1

HCID 69107640HCID 69107640, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a stirred solution of 3.39 g (53 mmol) of NaOEt in 30 mL of EtOH, at 0° C., was added dropwise 8.56 mL (53 mmol) of ethyl isobutyrylacetate (commercially available) in 10 mL of EtOH. The reaction mixture was stirred at room temperature for 40 minutes, and then 8.68 g (0.05 mol) solution of 3-fluoro-benzaldehyde-chloro-oxime (Prepared according to: J. Agric. Food Chem. 1995, 43, 219-228.) in 30 mL of EtOH was added dropwise in an ice-bath and the resulting suspension was stirred at room temperature for 2 h. The mixture was then evaporated and the residue partitioned between 200 mL of ethyl acetate and 100 mL of H2O. The aqueous phase was then separated and extracted with ethyl acetate (2×60 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4 and evaporated to give 15 g of crude product (purity ˜30%) as a yellow syrup. The crude product was used in the subsequent hydrolysis without purification.

Workup

  1. stirringthe resulting suspension was stirred at room temperature for 2 h
  2. customThe mixture was then evaporated
  3. customthe residue partitioned between 200 mL of ethyl acetate and 100 mL of H2O
  4. customThe aqueous phase was then separated
  5. extractionextracted with ethyl acetate (2×60 mL)
  6. washThe combined organic extracts were washed with brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-a1f0dfead33f407c9fb4fe1ca6eaf1ae
Source dataset
uspto-grants-2008_05
Patent number
US07378435B2

Reaction notes

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