反应详情

3.50 g (29.1 mM) of (R)-(+)-styrene oxide, 0.035 g of lithium chloride and 14 ml of N,N-dimethylformamide (DMF) were placed in a 50 ml-three necked flask. Under refluxing and stirring in nitrogen atmosphere, a solution of 4.38 g (29.4 mM) of 4-methoxyphenyl isocyanate in 3.5 ml of DMF was added dropwise to the mixture in 40 minutes, followed by refluxing for 40 minutes under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and recrystallized from methanol. The resultant crystal was purified by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1) and recrystallized from a toluene/methanol mixture solvent to obtain 4.22 g of (5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 53.8%). This compound showed the following phase transition series.

1. temperatureUnder refluxing
2. temperatureby refluxing for 40 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. customrecrystallized from methanol
9. customThe resultant crystal was purified by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1)
10. customrecrystallized from a toluene/methanol mixture solvent