Methyl iodide → 1-(1,2,4-Trimethyl-1H-pyrrol-3-yl)ethanone

HRID 1091153Notes

Reaction equation

HRID 1091153 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[CH:7][NH:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].I[CH3:14]>CN(C=O)C>[CH3:14][N:6]1[CH:7]=[C:8]([CH3:9])[C:4]([C:1](=[O:3])[CH3:2])=[C:5]1[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 24758Sodium hydride

Product 1

HCID 149872381-(1,2,4-Trimethyl-1H-pyrrol-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-acetyl-2,4-dimethylpyrrole (2.0 g) in dry DMF (30 ml) was added dropwise, with stirring, to a suspension of sodium hydride (78% dispersion in oil; 565 mg) in dry DMF (15 ml) at 0° under nitrogen and stirring was continued at room temperature for 1 h. Iodomethane (1.14 ml) was added dropwise at 0° and stirring was continued for 1.5 h. The suspension was evaporated, treated with 8% aqueous sodium bicarbonate (80 ml) and extracted with ethyl acetate (2×80 ml). The combined, dried organic extracts were evaporated to give a solid (2.1 g) which was dissolved in dichloromethane (20 ml) and adsorbed onto silica gel (Merck 7734, 6 g). This was applied to an FCC column and elution with System B (1:3) afforded the title compound (1.89 g) as crystals, m.p. 68°-70°.

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 h
  3. customThe suspension was evaporated
  4. additiontreated with 8% aqueous sodium bicarbonate (80 ml)
  5. extractionextracted with ethyl acetate (2×80 ml)
  6. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-28fb3d6e8f58472d938027b9b48108b5
Source dataset
uspto-grants-1992_01
Patent number
US05084474

Reaction notes

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