Reaktion #1340555

ord-632fe13c58be4ec886ff11dd65f31167

Reaktionsgleichung

O=C(O)C=Cc1cccc(C(F)(F)F)c1
3-(trifluoromethyl) cinnamic acid
CCO
ethanol
COC(=O)CCc1cccc(C(F)(F)F)c1
captioned compound
COC(=O)CCc1cccc(C(F)(F)F)c1
3-(3-trifluoromethylphenyl)-propionic acid methyl ester

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePalladium/carbon was separated by filtration
  2. 2
    Einengenthe filtrate was concentrated under reduced pressure
  3. 3
    workup.ADDITION20 ml of methanol and 4 drops of concentrated sulfuric acid were added
  4. 4
    workup.STIRRINGthe mixture was stirred at 60° C. for 2 hours
  5. 5
    workup.WAITleft
  6. 6
    Temperaturto cool down
  7. 7
    EinengenAfter concentration under reduced pressure, 20 ml of a saturated sodium bicarbonate aqueous solution
  8. 8
    workup.ADDITIONwas added
  9. 9
    Extraktionthe resultant was extracted with 20 ml of dichloromethane
  10. 10
    TrocknenThe extract was dried with anhydrous sodium sulfate
  11. 11
    Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 2.20 g of 3-(trifluoromethyl) cinnamic acid, 166 mg of palladium/carbon (10%, wet), and 40 ml of ethanol was stirred overnight under a hydrogen atmosphere at 1 atm. Palladium/carbon was separated by filtration, and the filtrate was concentrated under reduced pressure. 20 ml of methanol and 4 drops of concentrated sulfuric acid were added and the mixture was stirred at 60° C. for 2 hours, and then left to cool down. After concentration under reduced pressure, 20 ml of a saturated sodium bicarbonate aqueous solution was added, and the resultant was extracted with 20 ml of dichloromethane. The extract was dried with anhydrous sodium sulfate and then concentrated under reduced pressure to afford 2.40 g of the captioned compound as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08454978B2uspto-grants-2013_06