Water → 3-(4-Butylphenyl)-5-(4-methoxyphenyl)-2-oxazolidinone

HRID 54874

Reaction equation

HRID 54874 reaction equation
[Cl-].[Li+].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:5][CH3:6].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([CH:22]2[O:24][CH2:23]2)=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:23][CH:22]([C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:26][CH:25]=3)[O:24][C:14]2=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 980482-(4-Methoxyphenyl)oxiraneHCID 433294Lithium ChlorideHCID 27963134-Butylphenyl isocyanate

Product 1

HCID 199567023-(4-Butylphenyl)-5-(4-methoxyphenyl)-2-oxazolidinoneYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 20 ml-three necked flask, 0.013 g of lithium chloride and 3.8 ml of DMF were placed. To the mixture, a solution of 1.09 g (6.22 mM) of 4-butylphenyl isocyanate and 6.20 mM of optically active 4-methoxystyrene oxide in 1.3 ml of DMF was added dropwise in 12 minutes under refluxing and stirring in nitrogen atmosphere, followed by refluxing for 50 minutes under stirring. After the reaction, the reaction mixture was left standing for cooling, then poured into water, and subjected to extraction with ethyl acetate. The organic layer was washed with water, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain a residue The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=10/1) and recrystallized from methanol to obtain 0.29 g of optically active 3-(4-butylphenyl)-5-(4-methoxyphenyl)-2-oxazolidinone (Yield: 14.5%).

Workup

  1. temperatureunder refluxing
  2. temperatureby refluxing for 50 minutes
  3. stirringunder stirring
  4. customAfter the reaction
  5. waitthe reaction mixture was left
  6. temperaturefor cooling
  7. extractionsubjected to extraction with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. customevaporated under reduced pressure
  11. customto obtain a residue The residue
  12. customwas purified by silica gel column chromatography (eluent: toluene/ethyl acetate=10/1)
  13. customrecrystallized from methanol

Sources & evidence

ORD record
ord-911e781ae40e4f81bc059adeb5bc3892
Source dataset
uspto-grants-1997_04
Patent number
US05624600

Linked notes

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