Cyclohexanone, 3,3-dimethyl- → 3,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

HRID 1778935Notes

Reaction equation

HRID 1778935 reaction equation
[Li]CCCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1>O1CCCC1.CCOCC>[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]([CH2:6][N:7]2[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]2)([OH:20])[CH2:15]1

Participants

6

Reactant 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 866813303,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a cold (−78° C.) solution of nBuLi (12.48 mL) in tetrahydrofuran (40 mL) was added a solution of 1,5-dimethyl-1H-pyrazole (3.0 g) in tetrahydrofuran (3 mL) dropwise. After stirring for 1 hour, a solution of 3,3-dimethylcyclohexanone (3.94 g) in tetrahydrofuran (3 mL) was added dropwise, and the reaction was allowed to warm to 0° C. After stirring for 1 hour, the reaction mixture was diluted with ether (100 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with a gradient of 3% to 25% ethyl acetate in hexanes, gave the title compound.

Workup

  1. stirringAfter stirring for 1 hour
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography
  7. washeluting with a gradient of 3% to 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ead138bcae7344b19599ffd9d4595adb
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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