Pyrrole → Cyclohexyl(1H-pyrrol-2-yl)methanone

HRID 1844734Notes

Reaction equation

HRID 1844734 reaction equation
C[Mg+].[Br-].[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>CCOCC>[CH:9]1([C:15]([C:5]2[NH:4][CH:8]=[CH:7][CH:6]=2)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8027PyrroleHCID 75938Cyclohexanecarbonyl chlorideHCID 178418689HCID 178418689, compound

Product 1

HCID 13432026Cyclohexyl(1H-pyrrol-2-yl)methanoneYield 20%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of MeMgBr (99.3 mL, 298 mmol) in Et2O (500 mL) a solution of 1H-pyrrole (20 g, 298 mmol, dissolved in Et2O) was added dropwise at rt under N2. The mixture was heated to reflux for 30 min and cyclohexanecarbonyl chloride (43 g, 298 mmol) was added dropwise at −30° C. The reaction was refluxed for 30 min, quenched by slowly addition of sat. NH4Cl, diluted with EA and water, washed with (3×) water and once with brine. The organic layer was dried over Na2SO4, concentrated and purified by CC to obtain compound 25a (10 g, 20%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureThe reaction was refluxed for 30 min
  4. customquenched by slowly addition of sat. NH4Cl
  5. additiondiluted with EA and water
  6. washwashed with (3×) water and once with brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by CC

Sources & evidence

ORD record
ord-fe1e7cb7032e4e72b9a535f3a7ff3ff2
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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