Epibromohydrin → HCID 14652025, compound

HRID 1109524Notes

Reaction equation

HRID 1109524 reaction equation
C[O-].[Na+].[OH:4][C:5]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][N:6]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>CN(C)C=O>[O:21]1[CH2:20][CH:19]1[CH2:17][O:4][C:5]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:7][N:6]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 10942334Sodium MethoxideHCID 178431794HCID 178431794, compound

Product 1

HCID 14652025HCID 14652025, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.32 g of sodium methoxide were added to a solution of 6.00 g of 3-hydroxy-4-methyl-5-phenylisoxazole in 500 ml of dimethylformamide, and the mixture was stirred at room temperature for 10 minutes. 10.4 g of epibromohydrin were then added dropwise at room temperature to the mixture, and the mixture was stirred at room temperature for 48 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, eluted with a 2:1 by volume mixture of cyclohexane and ethyl acetate, to give 5.60 g of the title compound as colorless cotton-like crystals, melting at 87°-88° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hours
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. customthe residue was purified by column chromatography through silica gel
  4. washeluted with a 2:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-5a76208b1bf8412983502125e1494cab
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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