Acetone → HCID 10858051, compound

HRID 1725512Notes

Reaction equation

HRID 1725512 reaction equation
C[O-].[Na+].[C:4]([O:11][CH2:12][CH3:13])(=[O:10])[C:5]([O:7]CC)=O.[CH3:14][C:15]([CH3:17])=[O:16].Cl[C:19](=[N:25]O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:12]([O:11][C:4](=[O:10])[C:5]([C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:25][O:16][C:15]=1[CH3:17])=[O:7])[CH3:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7268Diethyl OxalateHCID 6816376Ethyl chloro(hydroximino)acetateHCID 10942334Sodium Methoxide

Product 1

HCID 10858051HCID 10858051, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
45 °C

Procedure

To a well stirred solution of sodium methoxide (10.5 g, 0.15 mol) in 100 mL of dry ethanol, diethyl oxalate (21 mL, 0.15 mol) was added dropwise and the mixture was warmed to 45° C. Then dry acetone (45 mL, 0.60 mol) was added and after 30 min the final mixture was refluxed for 3 hours and stirred at room temperature overnight. Finally solvent was removed and 100 mL of fresh dry ethanol were added. The mixture was cooled to, 0° C. and a solution of ethyl chloro(hydroximino)acetate (27.2 g, 0.18 mol) in 25 mL of dry ethanol was added dropwise. Then it was stirred at 0° C. for 30 min and at room temperature for 3 days. Finally solvent was removed and the crude thus obtained was partitioned between ethyl acetate and water. It was dried and solvent removed to yield the desired product (90%) as an orange oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customFinally solvent was removed
  3. addition100 mL of fresh dry ethanol were added
  4. temperatureThe mixture was cooled to, 0° C.
  5. stirringThen it was stirred at 0° C. for 30 min and at room temperature for 3 days
  6. customFinally solvent was removed
  7. customthe crude thus obtained
  8. customwas partitioned between ethyl acetate and water
  9. customIt was dried
  10. customsolvent removed

Sources & evidence

ORD record
ord-cfe09207d7414c30a3bc790d0f3daa20
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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