Epichlorohydrin → 3-(2,3-Epoxypropoxy)-5-phenylisoxazole

HRID 1109525Notes

Reaction equation

HRID 1109525 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[OH:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:15][N:14]=1>CN(C)P(=O)(N(C)C)N(C)C>[O:11]1[CH2:10][CH:9]1[CH2:7][O:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:15][N:14]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 178515569HCID 178515569, compound

Product 1

HCID 148844763-(2,3-Epoxypropoxy)-5-phenylisoxazoleYield 82%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

10.28 g of anhydrous potassium carbonate and 6.89 g of epichlorohydrin were added to a solution of 10.00 g of 3-hydroxy-5-phenylisoxazole in 50 ml of hexamethylphosphoric triamide, and the mixture was stirred at room temperature for 24 hours. At the end of this time, insoluble materials were removed by filtration from the reaction mixture, and 200 ml of ethyl acetate were added thereto. The mixture was then washed twice, each time with 200 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was then dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, eluted with a 4:1 by volume mixture of cyclohexane and ethyl acetate, to give 11.00 g (yield 82%) of the title compound as colorless needles, melting at 98°-99° C.

Workup

  1. customAt the end of this time, insoluble materials were removed by filtration from the reaction mixture, and 200 ml of ethyl acetate
  2. additionwere added
  3. washThe mixture was then washed twice
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel
  7. washeluted with a 4:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-2a339bee8c4d44af91b641cca4f8e42a
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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