Water → 2-Amino-2-(3,4-difluorophenyl)ethanol

HRID 1860401Notes

Reaction equation

HRID 1860401 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][O:12]C(=O)[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].O.[OH-].[K+]>C(O)C>[NH2:10][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH2:13][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 220487464-(3,4-Difluorophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 220488782-Amino-2-(3,4-difluorophenyl)ethanolYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (+)-4-(3,4-difluorophenyl)-oxazolidin-2-one (1.39 mmol, 0.27 g) in 5.0 mL ethanol was added 5.0 mL of water and pellets of potassium hydroxide (5.0 mmol, 0.28 g). The resulting solution was then heated to reflux overnight. The solvent was removed in vacuo and the resulting residue was extracted with EtOAc (2×50 mL). The organic extracts were washed with brine and the organic layer was dried over Na2SO4. It was filtered and the solvent was removed in vacuo to obtain (+)-2-amino-2-(3,4-difluorophenyl)-ethanol as a white solid (0.21 g, 87% yield).

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. extractionthe resulting residue was extracted with EtOAc (2×50 mL)
  5. washThe organic extracts were washed with brine
  6. dry with materialthe organic layer was dried over Na2SO4
  7. filtrationIt was filtered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e097559bb5af406fbfda4ee8edb6ed60
Source dataset
uspto-grants-2003_03
Patent number
US06531471B2

Reaction notes

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