Sodium hydride → 1-[1-(4-Methylphenyl)cyclopropyl]ethan-1-one

HRID 1359548Notes

Reaction equation

HRID 1359548 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[CH2:19])[C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1>CN(C)C=O>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16](=[O:18])[CH3:17])[CH2:4][CH2:19]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 180007733-(4-Methylphenyl)-3-buten-2-one

Product 1

HCID 180009341-[1-(4-Methylphenyl)cyclopropyl]ethan-1-oneYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

507 mg of sodium hydride (55% in paraffin oil) is introduced into 20 ml of dimethylformamide under nitrogen at 0° C., and 1.36 g of trimethylsulfonium iodide is added. After 30 minutes at this temperature, 845 mg of ketone 40 is added in drops to 4 ml of dimethylformamide. It is stirred for 1 more hour at 0° C., then quenched with sodium chloride solution, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane, 447 mg of title compound 41 is obtained as a colorless oil.

Workup

  1. customquenched with sodium chloride solution
  2. extractionextracted with ethyl acetate
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-630432dfe6c04560aac08fd46a02acde
Source dataset
uspto-grants-2003_07
Patent number
US06600058B1

Reaction notes

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