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

HRID 77024Notes

Reaction equation

HRID 77024 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 20286794Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl esterYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-43254763d3064c23884c9cb44e62cf07
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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