Sodium hydride → HCID 18000846, compound

HRID 1166624Notes

Reaction equation

HRID 1166624 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH2:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[CH2:22])[C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1)[CH2:9][CH2:10][CH3:11]>CN(C)C=O>[CH2:8]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:19](=[O:21])[CH3:20])[CH2:4][CH2:22]2)=[CH:16][CH:17]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 18000926HCID 18000926, compound

Product 1

HCID 18000846HCID 18000846, compoundYield 61.9%

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 1.38 g of trimethylsulfonium iodide is added. After 30 minutes at this temperature, 1.06 g of ketone 52 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, 702 mg of title compound 53 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-a84ad23f6bcc4394aa91e1be34821206
Source dataset
uspto-grants-2003_09
Patent number
US06613920B1

Reaction notes

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