反应详情

4 mg of lithium chloride and 1.0 ml of DMF were placed in a 20 ml-three necked flask. Under refluxing and stirring in nitrogen atmosphere, a solution of 0.97 g (3.92 mM) of 4-octyloxyphenyl isocyanate and 0.80 g (3.92 mM) of (-)-4-hexylstyrene oxide in 1.8 ml of DMF was added dropwise to the mixture in 5 minutes, followed by refluxing for 5 minutes under stirring. After the reaction, the reaction mixture was cooled to room temperature and poured into ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in a toluene-ethyl acetate mixture solvent, followed by drying with anhydrous sodium sulfate and evaporation under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from an acetone/methanol mixture solvent to obtain 0.25 g of optically active 3-(4-octylphenyl)-5-(4-hexylphenyl)-2-oxazolidinone (Yield: 14.1%). This compound showed the following phase transition series.

1. temperatureUnder refluxing
2. temperatureby refluxing for 5 minutes
3. stirringunder stirring
4. customAfter the reaction
5. customto precipitate a crystal
6. filtrationThe crystal was recovered by filtration
7. washwashed with water
8. dissolutiondissolved in a toluene-ethyl acetate mixture solvent
9. dry with materialby drying with anhydrous sodium sulfate and evaporation under reduced pressure
10. customto obtain a residue
11. customThe residue was purified by silica gel column chromatography
12. customrecrystallized from an acetone/methanol mixture solvent