2-Acetylpyrrole → (2E)-3-(Dimethylamino)-1-(1H-pyrrol-2-yl)-2-propen-1-one

HRID 2352166Notes

Reaction equation

HRID 2352166 reaction equation
[C:1]([C:4]1[NH:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].C(O[CH:14](N(C)C)[N:15]([CH3:17])[CH3:16])(C)(C)C>CCCCCC>[CH3:14][N:15]([CH3:17])/[CH:16]=[CH:2]/[C:1]([C:4]1[NH:5][CH:6]=[CH:7][CH:8]=1)=[O:3]

Participants

4

Reactant 2

HCID 140792-AcetylpyrroleHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 14346958(2E)-3-(Dimethylamino)-1-(1H-pyrrol-2-yl)-2-propen-1-oneYield 42.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 39.6 g of 2-acetylpyrrole and 104 ml (87.7 g) of tert-butoxy bis(dimethylamino)methane was heated on a steam bath for 20 minutes. The reaction was allowed to subside, then heating was continued for 6 hours. The mixture solidified then was slurried in hexane with chilling. The crude product was collected, washed with hexane and dried. The solid was dissolved in chloroform containing 5% methanol and filtered through magnesium silicate. The eluent was evaporated in vacuo and the residue was recrystallized from dichloromethane/hexane containing a small amount of methanol. The solid was collected, washed with hexane then dried in vacuo giving 25.1 g of the desired compound as yellow crystals, mp 192°-193° C. (dec.).

Workup

  1. temperaturewas heated on a steam bath for 20 minutes
  2. temperatureheating
  3. temperaturewith chilling
  4. customThe crude product was collected
  5. washwashed with hexane
  6. customdried
  7. dissolutionThe solid was dissolved in chloroform containing 5% methanol
  8. filtrationfiltered through magnesium silicate
  9. customThe eluent was evaporated in vacuo
  10. customthe residue was recrystallized from dichloromethane/hexane containing a small amount of methanol
  11. customThe solid was collected
  12. washwashed with hexane
  13. customthen dried in vacuo

Sources & evidence

ORD record
ord-66f0f7069de6448da927a01edbfa3044
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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