N,N-二甲基甲酰胺 → (5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone

HRID 54869

反应方程式

HRID 54869 反应方程式
[CH2:1]1[O:9][C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=O)=[CH:14][CH:13]=1.CN(C)C=[O:24]>[Cl-].[Li+]>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][C@@H:2]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[O:9][C:1]2=[O:24])=[CH:14][CH:13]=1

参与物

5

反应物 3

HCID 6228N,N-二甲基甲酰胺2 次HCID 79443对甲氧基苯异氰酸酯HCID 114705(R)-环氧苯乙烷

产物 1

HCID 53894593(5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone收率 53.8%

试剂、催化剂与溶剂 1

HCID 433294氯化锂催化剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-533bfd7a4c5d4057b5b495e5fffe3c3b
来源数据集
uspto-grants-1997_04
专利号
US05624600

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