Water → (5-Phenyl-1,2-oxazol-3-yl)methanol

HRID 384105Notes

Reaction equation

HRID 384105 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12](O)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C(=O)([O-])O.[Na+]>O1CCCC1.B.O1CCCC1>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1519165-Phenyl-3-isoxazolecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 1481082(5-Phenyl-1,2-oxazol-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-phenylisoxazol-3-carboxylic acid (551 mg) in tetrahydrofuran (15 ml), 3.7 ml of borane-tetrahydrofuran complex (1.17M tetrahydrofuran solution) was added, and the reaction solution was stirred at 80° C. for 10 hours. Water and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction solution, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-50:50)) to afford the title compound as a white solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-50:50))

Sources & evidence

ORD record
ord-a98cd7beb9034572938093d25c166f48
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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