Butyl bromide → N-n-butyl-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole

HRID 2107739Notes

Reaction equation

HRID 2107739 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](Br)[CH2:26][CH2:27][CH3:28]>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)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 148524113-(3,5-Di-t-butyl-4-hydroxybenzoyl)pyrrole

Product 1

HCID 14852415N-n-butyl-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 0.69 g of sodium hydride (50% in mineral oil) in 50 ml of anhydrous dimethylformamide under nitrogen. After 1 hour at 20° C., 0.8 ml of n-butyl bromide was added. Stirring was continued for an additional 18 hours at room temperature. 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 on a silica column (200 g) eluting with hexane:ethyl acetate (9:1). Crystallization from acetone-hexane gave 1.52 g of N-n-butyl-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole (mp 101°-103° C.).

Workup

  1. stirringStirring
  2. waitwas continued for an additional 18 hours at room temperature
  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 on a silica column (200 g)
  8. washeluting with hexane:ethyl acetate (9:1)
  9. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-2bd384b15d3543ffb5bed76da31c863d
Source dataset
uspto-grants-1990_06
Patent number
US04935440

Reaction notes

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