Epibromohydrin → 3-Methyl-5-[2-(2,3-epoxypropoxy)-styryl]-isoxazole

HRID 1659890Notes

Reaction equation

HRID 1659890 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[O:6][N:5]=1.[H][H].[CH2:20]([CH:22]1[O:24][CH2:23]1)Br>CS(C)=O>[CH3:3][C:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:20][CH:22]2[O:24][CH2:23]2)[O:6][N:5]=1

Participants

6

Reactant 4

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 8401643-Methyl-5-(2-hydroxy-styryl)-isoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 544956243-Methyl-5-[2-(2,3-epoxypropoxy)-styryl]-isoxazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

6.44 g of 55% strength sodium hydride in paraffin oil (0.15 mole) are introduced into 200 ml of absolute dimethylsulfoxide and 30 g (0.15 mole) of 3-methyl-5-(2-hydroxy-styryl)-isoxazole, dissolved in 50 ml of dimethylsulfoxide, are added dropwise, at room temperature. When the evolution of hydrogen has ceased, 20.2 g (0.15 mole) of epibromohydrin are added dropwise and the reaction mixture is stirred for 20 hours at room temperature. It is then poured onto 1.5 liters of ice water and the solid residue is filtered off and recrystallized from isopropanol. 26.2 g (68% of theory) of colorless crystals, of melting point 99°-100° C., are obtained.

Workup

  1. additionare added dropwise, at room temperature
  2. filtrationthe solid residue is filtered off
  3. customrecrystallized from isopropanol
  4. custom26.2 g (68% of theory) of colorless crystals, of melting point 99°-100° C., are obtained

Sources & evidence

ORD record
ord-af3d5ea95d264301830bdf3d907ae66c
Source dataset
uspto-grants-1981_12
Patent number
US04305951

Reaction notes

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