Diethyl Oxalate → Ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate

HRID 747581Notes

Reaction equation

HRID 747581 reaction equation
[O-]CC.[Na+].C(O[C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19]([C:23](=[O:25])C)[CH:20]=[CH:21][CH:22]=1>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:23](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:26])[F:27])[CH:18]=1)[CH3:13]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 676823'-(Trifluoromethyl)acetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 2063905Ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 1.96 g (0.0275 mol) sodium ethoxide (95%) and 22 ml ethanol was stirred 20 minutes at room temperature and was then cooled with an ice bath. 3.65 g (0.025 mol) diethyloxalate followed by 4.7 g (0.025 mol) 1-(3-trifluoromethyl-phenyl)-ethanone were added slowly. The mixture was stirred for 30 min. at 0-5° C., then allowed to warm to room temperature and additional 25 ml ethanol were added. After 1 d at room temperature the solvent was evaporated. Water and diethylether were added to the residue. The organic phase was separated and the aqueous phase was extracted one more time with diethyl ether. The aqueous phase was acidified with 2M HCl to pH2 and extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulfate, the solvent was evaporated and the residue triturated with petrol ether to give 5.35 g (0.0185 mol) 3-oxo-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester.

Workup

  1. temperaturewas then cooled with an ice bath
  2. additionwere added slowly
  3. stirringThe mixture was stirred for 30 min. at 0-5° C.
  4. temperatureto warm to room temperature
  5. customAfter 1 d at room temperature the solvent was evaporated
  6. additionWater and diethylether were added to the residue
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was extracted one more time with diethyl ether
  9. extractionextracted three times with diethyl ether
  10. dry with materialThe combined organic phases were dried over magnesium sulfate
  11. customthe solvent was evaporated
  12. customthe residue triturated with petrol ether

Sources & evidence

ORD record
ord-4fcbb30a30734e30b3cfba33dbc6f04e
Source dataset
uspto-grants-2008_07
Patent number
US07396944B2

Reaction notes

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