(3-Phenyl-5-isoxazolyl)methanol → 3-Phenyl-1,2-oxazole-5-carbaldehyde

HRID 868924

Reaction equation

HRID 868924 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][OH:13])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=[O:13])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2763417(3-Phenyl-5-isoxazolyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-phenylisoxazol-5-yl)methanol (0.9 g, 5.1 mmol) in DCM (10 mL) was added pyridinium chlorochromate (PCC) (2.1 g, 10.2 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with water, extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give 3-phenylisoxazole-5-carbaldehyde as a light yellow solid (600 mg).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solution was then concentrated under vacuum

Sources & evidence

ORD record
ord-3f01702367b44dc4b6811f1ac489c814
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

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