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

HRID 1413840Notes

Reaction equation

HRID 1413840 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-hydroxystyryl)-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. The mixture is then poured onto 1.5 liters of ice water and the solid precipitate is filtered off and recrystallized from isopropanol. 26.2 g (68% of theory) of colorless crystals, melting point 99°-100° C.

Workup

  1. additionare added dropwise at room temperature
  2. filtrationthe solid precipitate is filtered off
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-80da21076aab482995194cc490b43895
Source dataset
uspto-grants-1981_02
Patent number
US04251539

Reaction notes

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