(R)-4-Benzyl-2-oxazolidinone → (R)-4-Benzyl-3-pent-4-enoyloxazolidin-2-one

HRID 1013831Notes

Reaction equation

HRID 1013831 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](Cl)(=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18].C([Li])CCC>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 42284934-Pentenoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 10858190(R)-4-Benzyl-3-pent-4-enoyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve (R)-4-Benzyl-2-oxazolidinone (5.906 g, 33.33 mmoles) and 4-Pentenoyl chloride (4.54 g, 38.33 mmoles) in THF (50 mL). Cool the mixture in a dry ice acetone bath, and add n-Butyl Lithium (36.66 mmoles; 14.66 mL; 10.12 g) dropwise at −78° C. Stir the mixture at −78° C. for 30 min and then warm to ambient temperature. Quench the solution with 60 ml of sat. ammonium chloride, and then extract with 60 ml MTBE. Separate the organics and dry over magnesium sulfate. Filter the drying agent and concentrate under vacuum to an oil (6.96 g). LCMS=100% 260 amu (M+1).

Workup

  1. temperatureCool the mixture in a dry ice acetone bath
  2. temperaturewarm to ambient temperature
  3. customQuench the solution with 60 ml of sat. ammonium chloride
  4. extractionextract with 60 ml MTBE
  5. customSeparate the organics and
  6. dry with materialdry over magnesium sulfate
  7. filtrationFilter the drying agent
  8. concentrationconcentrate under vacuum to an oil (6.96 g)

Sources & evidence

ORD record
ord-445ebb5b678248ffb3d2c1117c6c1cd5
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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