Ethyl Acetoacetate → HCID 66769567, compound

HRID 595082Notes

Reaction equation

HRID 595082 reaction equation
CO[Na].[CH2:4]([O:6][C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10])C.C([O:15][C:16](=O)[CH:17]=[CH:18][CH3:19])C>CO>[CH3:4][O:6][C:7]([C:8]1[CH:18]([CH3:19])[CH2:17][C:16](=[O:15])[CH2:10][C:9]=1[OH:11])=[O:12]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 121912-Butenoic acid, ethyl esterHCID 178418582HCID 178418582, compound

Product 1

HCID 66769567HCID 66769567, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a freshly prepared solution of MeONa (432 g, 7.99 mol) in MeOH (2 L) is added 3-oxo-butyric acid ethyl ester (1.04 kg, 7.99 mol) over 15 min and the mixture is stirred on an ice bath for an additional 15 min. But-2-enoic acid ethyl ester (912 g, 7.99 mol) is added dropwise at RT and the mixture stirred at RT for 1 h and then the reaction mixture is refluxed for 2 h. After cooling to RT, the precipitated solids are filtered off, dissolved in cold water (1.5 L), acidified with HCl (3 M) to pH to 7 and the resulting mixture is extracted with EtOAc (4×800 mL). The combined organic phase is dried over anhydrous Na2SO4, the solvents are evaporated in vacuo and the residue recrystallized from hexane to give 2-hydroxy-6-methyl-4-oxo-cyclohex-1-enecarboxylic acid methyl ester (672 g, 42% yield).

Workup

  1. stirringthe mixture stirred at RT for 1 h
  2. temperaturethe reaction mixture is refluxed for 2 h
  3. filtrationthe precipitated solids are filtered off
  4. dissolutiondissolved in cold water (1.5 L)
  5. extractionthe resulting mixture is extracted with EtOAc (4×800 mL)
  6. dry with materialThe combined organic phase is dried over anhydrous Na2SO4
  7. customthe solvents are evaporated in vacuo
  8. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-63def54fa5b04e26933331bdf98c9d59
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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