[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]=16.44 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.
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