Methyl iodide → HCID 14852413, compound

HRID 2107737Notes

Reaction equation

HRID 2107737 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[C:8]([C:10]1[CH:14]=[CH:13][NH:12][CH:11]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH3:25][N:12]1[CH:13]=[CH:14][C:10]([C:8](=[O:9])[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)=[CH:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 148524113-(3,5-Di-t-butyl-4-hydroxybenzoyl)pyrrole

Product 1

HCID 14852413HCID 14852413, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 G (6.6 mmol) of 3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole were added to a stirred suspension of 640 mg (13 mmol) of sodium hydride (50% in mineral oil) in 20 ml of anhydrous dimethylformamide. After 1 hour at room temperature, 0.415 ml (6.68 mmol) of methyl iodide was added, and stirring at room temperature was continued for an additional hour. Nitrogen was then bubbled through the reaction mixture for 10 minutes and thereafter the reaction mixture was partitioned between methylene chloride and water. The organic phase was washed with water, dried and evaporated in vacuo. Purification of the crude product by t.l.c. using hexane:ethyl acetate (80:20) afforded 1.439 g (69%) of the title compound, which was recrystallized from methylene chloride-hexane (mp 135.5°-136.5° C.).

Workup

  1. waitwas continued for an additional hour
  2. customNitrogen was then bubbled through the reaction mixture for 10 minutes
  3. customthe reaction mixture was partitioned between methylene chloride and water
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customPurification of the crude product by t.l.c

Sources & evidence

ORD record
ord-fbee9abc8e70494e818a698d49e49574
Source dataset
uspto-grants-1990_06
Patent number
US04935440

Reaction notes

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