Methyl iodide → HCID 14852027, compound

HRID 1032830Notes

Reaction equation

HRID 1032830 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])([CH3:5])[CH3:4].I[CH3:25]>O>[C:3]([C:7]1[CH:8]=[C:9]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[CH:10]=[C:11]([C:14]([CH3:16])([CH3:17])[CH3:15])[C:12]=1[O:13][CH3:25])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6918219HCID 6918219, compound

Product 1

HCID 14852027HCID 14852027, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 0.3 g (7.5 mmol) of 60% sodium hydride in a mineral dispersion previously washed with hexane, in 20 ml of dimethylsulfoxide, there was added 2 g (6.9 mmol) of 1-(3,5-di-tert-butyl-4-hydroxyphenyl)pyrrolidin-2-one. Gas evolution was observed. Twenty minutes later, 1 g (7 mmol) of iodomethane was added. The reaction mixture was stirred for thirty minutes and then diluted with 70 ml of water. The precipitated solid was collected by filtration and recrystallized from acetonehexane to yield 1.7 g (5.6 mmol) of 1-(3,5-di-tert-butyl-4-methoxyphenyl)pyrrolidin-2-one, melting point 90°-91° C.

Workup

  1. washpreviously washed with hexane, in 20 ml of dimethylsulfoxide
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from acetonehexane

Sources & evidence

ORD record
ord-a09bd02690cd4f3c9a2d606cc7025a9c
Source dataset
uspto-grants-1990_09
Patent number
US04959482

Reaction notes

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