Ethyl alpha-oxo-4-(trifluoromethyl)benzeneacetate → Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl ester

HRID 1255057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255057
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[BH4-].[Na+]>CCO>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([OH:1])[C:8]1[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=1)[CH3:7]

Komponenten

4

Edukt 2

HCID 2774410Ethyl alpha-oxo-4-(trifluoromethyl)benzeneacetateHCID 4311764Sodium borohydride

Produkt 1

HCID 20286794Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl esterAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 2-oxo-2-(4-(trifluoromethyl)phenyl)acetate (500 mg, 2.03 mmol) is dissolved in absolute EtOH (10 mL) and cooled at 0° C. under N2. NaBH4 (38.4 mg, 1.02 mmol) is added in two portions and the resulting suspension is allowed to warm to RT and stirred for 45 minutes. The solvent is evaporated, the resulting residue is diluted with Et2O and cool water is added. The organic layer is separated, washed with water and brine, dried over Na2SO4, filtered and evaporated obtaining intermediate I149 as a colorless oil (440 mg, 87% yield).

Aufarbeitung

  1. temperatureto warm to RT
  2. customThe solvent is evaporated
  3. additionthe resulting residue is diluted with Et2O
  4. temperaturecool water
  5. additionis added
  6. customThe organic layer is separated
  7. washwashed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5929906ad77f43998a7e3967d55f1661
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455646B2

Notizen zur Reaktion

Wird geladen…