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

HRID 1430303Notes

Reaction equation

HRID 1430303 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-0850d3905edb41dd9471ef060a45ff64
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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