Methyl iodide → HCID 14852027, compound

HRID 1613275Notes

Reaction equation

HRID 1613275 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 acetone-hexane 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 acetone-hexane

Sources & evidence

ORD record
ord-27468d734a8a4467b71cf3d693c8f1d1
Source dataset
uspto-grants-1993_03
Patent number
US05192791

Reaction notes

Loading…