Methyl iodide → HCID 67715428, compound

HRID 974881Notes

Reaction equation

HRID 974881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:13]2[CH2:17][O:16][C:15](=[O:18])[NH:14]2)[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:21]I>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:13]2[CH2:17][O:16][C:15](=[O:18])[N:14]2[CH3:21])[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67715624HCID 67715624, compound

Product 1

HCID 67715428HCID 67715428, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4(S)-(1(S)-(3,4-dichlorophenyl)-3-butenyl)-2-oxazolidinone (3.25 g, 11.4 mmol) in DMF (25 mL) at room temp was added NaH (573 mg, 95%, 22.7 mmol). The mixture was stirred for 20 min whereupon MeI (3.54 mL, 57.0 mmol) freshly filtered through basic alumina was added and the resultant reaction mixture was stirred at 70° C. for 14 h. The cooled reaction mixture was diluted with H2O (250 mL) and extracted with EtOAc (3×125 mL). The combined organic extracts were washed with H2O (3×100 mL), brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 1-5% MeOH/CH2Cl2) to afford the title compound (2.93 g, 86%) as a colorless solid and recovered starting material (382 mg, 11%).

Workup

  1. filtrationfreshly filtered through basic alumina
  2. additionwas added
  3. customthe resultant reaction mixture
  4. customThe cooled reaction mixture
  5. extractionextracted with EtOAc (3×125 mL)
  6. washThe combined organic extracts were washed with H2O (3×100 mL), brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica gel 60, 1-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4e6df39f3d204015b3b25503b515fbf4
Source dataset
uspto-grants-1997_03
Patent number
US05607936

Reaction notes

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