Methyl iodide → Cyclohexyl(1H-pyrrol-2-yl)methanone

HRID 1389130Notes

Reaction equation

HRID 1389130 reaction equation
CI.[Mg].[NH:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.[CH:9]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl-].[NH4+]>CCOCC.O>[NH:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:15]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:16]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 8027PyrroleHCID 25517Ammonium ChlorideHCID 75938Cyclohexanecarbonyl chlorideHCID 5462224Magnesium

Product 1

HCID 13432026Cyclohexyl(1H-pyrrol-2-yl)methanoneYield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Methyl iodide (42.60 g.) in dry ether (150 ml.) was added to a stirred mixture of magnesium turnings (7.30 g.) in dry ether (50 ml.) at such a rate that gentle reflux was maintained. After completion of the addition the mixture was stirred at room temperature for 30 minutes and then pyrrole (20.13 g., 0.44 mole) was added at such a rate that gentle reflux was maintained. After completion of the addition the mixture was heated under reflux with stirring for 30 minutes and then cooled to 0° C. A solution of cyclohexane carboxylic acid chloride (44.0 g., 0.30 mole) in dry ether (100 ml.) was added dropwise with stirring and the resulting mixture was heated under reflux with stirring for 30 minutes. The mixture was cooled and a solution of ammonium chloride (20 g.) in water (200 ml.) was added with stirring. The organic layer was separated, washed once with 0.5 N sodium hydroxide solution (50 ml.), twice with water (100 ml.) and dried over sodium sulphate. The ether was evaporated to give a viscous oil which was distilled to give cyclohexyl pyrrol-2-yl ketone (31.5 g.), B.P. 162°-165° at 15 mm., M.P. 83°-84°.

Workup

  1. temperaturethat gentle reflux
  2. temperaturewas maintained
  3. additionAfter completion of the addition the mixture
  4. temperaturethat gentle reflux
  5. temperaturewas maintained
  6. additionAfter completion of the addition the mixture
  7. temperaturewas heated
  8. temperatureunder reflux
  9. stirringwith stirring for 30 minutes
  10. temperaturecooled to 0° C
  11. stirringwith stirring
  12. temperaturethe resulting mixture was heated
  13. temperatureunder reflux
  14. stirringwith stirring for 30 minutes
  15. temperatureThe mixture was cooled
  16. stirringwith stirring
  17. customThe organic layer was separated
  18. washwashed once with 0.5 N sodium hydroxide solution (50 ml.), twice with water (100 ml.)
  19. dry with materialdried over sodium sulphate
  20. customThe ether was evaporated
  21. customto give a viscous oil which
  22. distillationwas distilled

Sources & evidence

ORD record
ord-a3459aed3a564223ae9881be9158b8b2
Source dataset
uspto-grants-1981_01
Patent number
US04243672

Reaction notes

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