Isopropanol → 3-Benzoyl-5-propionylisoxazole

HRID 1440326Notes

Reaction equation

HRID 1440326 reaction equation
[C:1]([C:9]1[CH:13]=[C:12]([CH:14]([OH:17])[CH2:15][CH3:16])[O:11][N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=C(C(=O)CC)ON=1.C(O)(C)C>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>[C:1]([C:9]1[CH:13]=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[O:11][N:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 138021011-(3-Bromo-5-isoxazolyl)-1-propanoneHCID 199769423-Benzoyl-5-(1-hydroxypropyl)isoxazole

Product 1

HCID 199769473-Benzoyl-5-propionylisoxazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 131709961Jones' reagentSolvent

Procedure

Reacted under reflux for 2 hours were 5.0 g (27.3 mmol) of benzoylacetohydroxamoyl chloride prepared by a known process [J.Org.Chem., 409 (1942)] and 5.0 g (59.5 mmol) of 1-pentyne-3-ol. The reaction mixture was added into water, followed by extraction with ethyl ether. The extract was concentrated and then purified by silica gel chromatography (eluent: chloroform), whereby the title compound, namely, 3-benzoyl-5-(1-hydroxypropyl)isoxazole was obtained. It was dissolved in acetone, to which the Jones' reagent was added dropwise under ice cooling so that it was oxidized from the alcohol form to a ketone form. Isopropyl alcohol was added to the reaction mixture. After an insoluble material was filtered off, the solvent was distilled off so that 3-benzoyl-5-propionylisoxazole was obtained as colorless crystals.

Workup

  1. additionwas added dropwise under ice cooling so that it
  2. filtrationAfter an insoluble material was filtered off
  3. distillationthe solvent was distilled off so that 3-benzoyl-5-propionylisoxazole
  4. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-9321e80454e349619639f590d3430d72
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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