Cyclooctanone → 1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

HRID 336613Notes

Reaction equation

HRID 336613 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:21])[CH2:20][CH2:19][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:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 10403CyclooctanoneHCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 866812711-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a cold (−78° C.) solution of n-butyllithium (10 mL, 2.5M) in tetrahydrofuran (20 mL) was added 1,5-dimethyl-1H-pyrazole (2.0 g) in tetrahydrofuran (10 mL) dropwise via syringe. After 1 hour, cyclooctanone (2.63 g) in tetrahydrofuran (5 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 twice with additional ethyl acetate. The combined organics were dried over Na2SO4, filtered, and concentrated to provide the 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 twice with additional ethyl acetate
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ee156e0504b4829b44c46e22f549efd
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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