Methyl iodide → HCID 10550935, compound

HRID 1532752Notes

Reaction equation

HRID 1532752 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:31]=[CH:30][C:19]([CH2:20][CH:21]([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=1.[H-].[Na+].[CH3:34]I.S([O-])(O)(=O)=O.[Na+]>CN(C)C=O>[CH3:34][C:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:31][CH:30]=1)([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 6918417HCID 6918417, compound

Product 1

HCID 10550935HCID 10550935, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylmalonate (4.24 g, 10.0 mmol) synthesized according to the method described in WO95/18125 was dissolved in dimethylformamide (40 ml), and sodium hydride (60% in oil, 480 mg, 12.0 mmol) was added at 0° C., which was followed by stirring for 2 hr. Methyl iodide (0.93 ml, 15.0 mmol) was added at room temperature and, 2.5 hours later, 1N sodium hydrogensulfate (100 ml) was added. The mixture was extracted three times with ethyl acetate. The extracted organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness to give a crude title compound, which was purified and concentrated by silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1→7:1→5:1) to give the title compound (2.71 g, yield 62%) as a white solid.

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. washThe extracted organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customto give a crude title compound, which
  6. customwas purified
  7. concentrationconcentrated by silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1→7:1→5:1)

Sources & evidence

ORD record
ord-b2514f93bfd047049c93f1cee7b3082a
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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