Iodoethane → N-ethyl-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole

HRID 2107738Notes

Reaction equation

HRID 2107738 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+].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:25]([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)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 148524113-(3,5-Di-t-butyl-4-hydroxybenzoyl)pyrrole

Product 1

HCID 14852414N-ethyl-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole

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 cooled, stirred suspension of 0.70 g of sodium hydride (50% in mineral oil) in 50 ml of anhydrous dimethylformamide under nitrogen. After 30 minutes at room temperature, 0.7 ml of ethyl iodide was added, and stirring at room temperature was continued for an additional 2 hours. The reaction mixture was poured over a 10% HCl-ice mixture, then extracted three times with 250 ml ethyl acetate. The organic layer was washed five times with 200 ml water, dried and evaporated to dryness. The residue was purified by chromatography on alumina (3% water, 100 g) eluting with hexane:ethyl acetate (9:1). Crystallization from methylene chloride-hexane gave 1.11 g of N-ethyl-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole (mp 73°-75° C.).

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for an additional 2 hours
  3. extractionextracted three times with 250 ml ethyl acetate
  4. washThe organic layer was washed five times with 200 ml water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on alumina (3% water, 100 g)
  8. washeluting with hexane:ethyl acetate (9:1)
  9. customCrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-1bf9fc87377c4bc2b02d48d97f4fbab5
Source dataset
uspto-grants-1990_06
Patent number
US04935440

Reaction notes

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