Sodium borohydride → HCID 57800077, compound

HRID 1694641Notes

Reaction equation

HRID 1694641 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([C:14](OCC)=[O:15])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+]>C(O)C>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH2:14][OH:15])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53439058Ethyl 5-[3-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxylate

Product 1

HCID 57800077HCID 57800077, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 5-[3-(trifluoromethyl)phenyl]isoxazole-3-carboxylate (2 g, 7 mmol) in ethanol (70 mL) in an ice bath was added sodium borohydride (1.06 g, 28 mmol) portionwise. The resulting mixture was stirred at room temperature for 1.5 hours, which was then quenched with saturated ammonium chloride aqueous solution. Solvent was removed from the mixture under reduced pressure, and the residue was dissolved in ethyl acetate and washed with water. The organic layer was then dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=2:3) to afford {5-[3-(trifluoromethyl)phenyl]isoxazol-3-yl}methane-1-ol.

Workup

  1. customwhich was then quenched with saturated ammonium chloride aqueous solution
  2. customSolvent was removed from the mixture under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was then dried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=2:3)

Sources & evidence

ORD record
ord-87273f60050641de958f51eba6d1818a
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

Loading…