Diethyl Oxalate → HCID 178473097, compound

HRID 251950Notes

Reaction equation

HRID 251950 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[O:5])[CH3:4].[C:7](OCC)(=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[O-]CC.[Na+]>C(O)C>[OH:5][C:3]([CH:2]([CH3:6])[CH3:1])=[CH:4][C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 112513-Methyl-2-butanoneHCID 2723922Sodium ethoxide

Product 1

HCID 178473097HCID 178473097, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 17.2 g of 3-methyl-2-butanone, 27.1 g of diethyl oxalate and 130 ml of ethanol was added 95 ml of sodium ethoxide (20% ethanol solution), and the resulting mixture was stirred at 60° C. for 5 hours. After allowed to cool to room temperature, a deposited precipitate was collected by filtration and washed with ethanol. The filter cake was partitioned between 2N hydrochloric acid and methyl t-butyl ether. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 28.8 g of ethyl 4-hydroxy-5-methyl-2-oxo-3-hexenoate of the formula:

Workup

  1. temperatureto cool to room temperature
  2. filtrationa deposited precipitate was collected by filtration
  3. washwashed with ethanol
  4. customThe filter cake was partitioned between 2N hydrochloric acid and methyl t-butyl ether
  5. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f36e006c6a084c8198e9e2677107df94
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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