Methyl iodide → HCID 18361970, compound

HRID 382799Notes

Reaction equation

HRID 382799 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14]2)=[CH:7][C:6]=1[O:19][CH3:20])[CH3:4].[CH3:21]I>O1CCCC1.CN(C)C=O>[CH2:3]([C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([CH:13]2[CH2:17][N:16]([CH3:21])[C:15](=[O:18])[CH2:14]2)=[CH:9][C:10]=1[O:11][CH3:12])[CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18361990HCID 18361990, compound

Product 1

HCID 18361970HCID 18361970, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.12 g (78 mmol) of a sodium hydride dispersion (60% in oil) were added using a spatula and while stirring to a suspension of 8.85 g (35.5 mmol) of 4-(4-ethyl-3,5-dimethoxy-phenyl)-pyrrolidin-2-one in 250 ml of tetrahydrofuran and 2 ml of dimethylformamide and the mixture was stirred at room temperature for a further hour. Thereafter, the reaction mixture was treated with 3.52 ml (106.5 mmol) of methyl iodide and left to stir at room temperature for a further 16 hours. Subsequently, the reaction mixture was poured on to 400 ml of ice-water and extracted twice with 600 ml of ethyl acetate each time. The combined organic phases were washed twice with 300 ml of saturated sodium chloride solution each time, dried (MgSO4) and concentrated in a vacuum. The crude product was purified by column chromatography on silica gel (methylene chloride/methanol 39:1). 8.08 g (86%) of 4-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-pyrrolidin-2-one were obtained as a beige solid.

Workup

  1. waitleft
  2. stirringto stir at room temperature for a further 16 hours
  3. extractionextracted twice with 600 ml of ethyl acetate each time
  4. washThe combined organic phases were washed twice with 300 ml of saturated sodium chloride solution each time
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in a vacuum
  7. customThe crude product was purified by column chromatography on silica gel (methylene chloride/methanol 39:1)

Sources & evidence

ORD record
ord-8fadee416ea14654905249feac7aaff5
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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