Calcium hypochlorite → 5-Propionyl-3-phenylisoxazole

HRID 1613870Notes

Reaction equation

HRID 1613870 reaction equation
[OH:1][CH:2]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)[CH2:3][CH3:4].Cl.N1C=CC=CC=1.Cl[O-].[Ca+2].Cl[O-]>ClCCl>[C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)(=[O:1])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24504Calcium hypochloriteHCID 10176127Pyridinium chlorideHCID 151807655-(1-Hydroxypropyl)-3-phenylisoxazole

Product 1

HCID 151807665-Propionyl-3-phenylisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of dichloromethane, 1.0 g (5.0 mmol) of 5-(1-hydroxypropyl)-3-phenylisoxazole was dissolved. To the solution were added 100 mg (0.9 mmol) of pyridine hydrochloride, followed by the further addition of 1.4 g (9.9 mmol) of calcium hypochlorite. They were reacted at room temperature for 5 hours. After completion of the reaction, insoluble matter was filtered off and the organic layer wa washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was then recrystallized from ethanol, whereby the target compound, namely, 5-propiony-3-phenylisoxazole was obtained as crystals.

Workup

  1. customThey were reacted at room temperature for 5 hours
  2. customAfter completion of the reaction, insoluble matter
  3. filtrationwas filtered off
  4. washthe organic layer wa washed with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was then recrystallized from ethanol, whereby the target compound

Sources & evidence

ORD record
ord-5c298b398c314b51b92ce22d11d78a78
Source dataset
uspto-grants-1993_03
Patent number
US05194606

Reaction notes

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