Cyclohexanone → HCID 63960715, compound

HRID 337929Notes

Reaction equation

HRID 337929 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.CN(C)CCN(C)C.C([Li])CCC.[C:20]1(=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1.O>[CH3:1][N:2]1[C:6]([C:20]2([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 702551H-Pyrazole, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 63960715HCID 63960715, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-methylpyrazole (6.0 g, 73.1 mmol) and N,N,N′,N′-tetramethylethylenediamine (10.96 mL, 73.1 mmol) in THF (125 mL), butyl lithium (2.69 M solution in hexane; 31.8 mL, 85.5 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 30 minutes. Then, cyclohexanone (9.06 mL, 87.7 mmol) was added thereto, and the mixture was stirred at room temperature for 15 hours. To the reaction solution, water (500 mL) was added, followed by extraction with ethyl acetate (250 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=3:2), to yield the title compound (11.32 g, 86%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. extractionfollowed by extraction with ethyl acetate (250 mL)
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-9f104c8c65d94aaa96dbb40fbb20e825
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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