Cyclohexanone → 1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

HRID 1778912Notes

Reaction equation

HRID 1778912 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCCC1>[CH3:12][C:11]1[N:7]([CH2:6][C:13]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 866813261-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a cold (−78° C.) solution of n-butyllithium (25 mL, 2.5M) in tetrahydrofuran (30 mL) was added 1,5-dimethyl-1H-pyrazole (5.0 g) in tetrahydrofuran (20 mL) dropwise via syringe. After 1 hour, cyclohexanone (5.1 g) in tetrahydrofuran (20 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous layer was extracted with additional ethyl acetate (twice). The combined organics were dried over Na2SO4, filtered, and concentrated to provide the crude title compound.

Workup

  1. customThe mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (twice)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7161acf79db403e932f0f0a09aa9d4c
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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