2-Acetylimidazole → 2-Acetyl-4-(4-pyridyl)cyclohexanone

HRID 231218Notes

Reaction equation

HRID 231218 reaction equation
C([Li])CCC.[N:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[C:19](C1NC=CN=1)(=[O:21])[CH3:20]>O1CCCC1.C(NC(C)C)(C)C.CCCCCC>[C:19]([CH:14]1[CH2:13][CH:12]([C:9]2[CH:10]=[CH:11][N:6]=[CH:7][CH:8]=2)[CH2:17][CH2:16][C:15]1=[O:18])(=[O:21])[CH3:20]

Participants

7

Reactant 3

HCID 5389722-AcetylimidazoleHCID 10154273Cyclohexanone, 4-(4-pyridinyl)-HCID 178418339Butyllithium

Product 1

HCID 137720552-Acetyl-4-(4-pyridyl)cyclohexanoneYield 66.5%

Reagents, catalysts & solvents 3

HCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

In 40 ml of tetrahydrofuran was dissolved 3.2 ml of diisopropylamine and, 14.2 ml of 1.6 mol n-butyl lithium solution in hexane was added to the solution at -20° C. Next, a solution of 2 g of 4-(4-pyridyl)cyclohexanone obtained in Example 1 in 40 ml of tetrahydrofuran was added to the mixture at -40° C. The reaction solution was cooled to -78° C., to which a solution of 2.5 g of acetylimidazole in 40 ml of tetrahydrofuran was added. After stirring at room temperature, the reaction solution was poured onto ice. After washing with ether, the aqueous phase was saturated with ammonium chloride and extracted with methylene chloride to give 1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone.

Workup

  1. additionwas added to the solution at -20° C
  2. additionwas added
  3. additionthe reaction solution was poured onto ice
  4. washAfter washing with ether
  5. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-44a6420d6be14772a5f09eb535096adb
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

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