Chromic Acid → 5-Propionyl-3-phenylisoxazole

HRID 1450638Notes

Reaction equation

HRID 1450638 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].[Cr](O)(O)(=O)=O>C(O)(=O)C.O>[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 2

HCID 24425Chromic AcidHCID 151807655-(1-Hydroxypropyl)-3-phenylisoxazole

Product 1

HCID 151807665-Propionyl-3-phenylisoxazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In 130 ml of acetic acid, 19 g (93.6 mmol) of 5-(1-hydroxypropyl)-3-phenylisoxazole were dissolved. A solution which had been obtained by dissolving 6.4 g (64 mmol) of chromic acid in a mixed solution of 50 ml of acetic acid and 10 ml of water was added dropwise. The reaction mixture was heated at 60° C. for 3 hours and the solvent was distilled off under reduced pressure. The residue thus obtained was poured in ice water. Colorless crystals precipitated were collected by filtration and then dried under reduced pressure. The crystals were purified by chromatography on a silica gel (eluent: 2:8 hexane/chloroform), whereby 5-propionyl-3-phenylisoxazole was obtained as colorless crystals.

Workup

  1. customA solution which had been obtained
  2. additionwas added dropwise
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue thus obtained
  5. customColorless crystals precipitated
  6. filtrationwere collected by filtration
  7. customdried under reduced pressure
  8. customThe crystals were purified by chromatography on a silica gel (eluent: 2:8 hexane/chloroform)

Sources & evidence

ORD record
ord-1f78464da91a4d619699984b4121eec8
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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