Acetone cardice → 1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl-methanol

HRID 1740102Notes

Reaction equation

HRID 1740102 reaction equation
C(=O)=O.CC(C)=O.C[O:9][C:10]([C:12]1[C:13]([CH2:28][CH3:29])=[N:14][N:15]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([Br:26])=[CH:21][C:20]=2[CH3:27])[C:16]=1[CH2:17][CH3:18])=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Br:26][C:22]1[CH:21]=[C:20]([CH3:27])[C:19]([N:15]2[C:16]([CH2:17][CH3:18])=[C:12]([CH2:10][OH:9])[C:13]([CH2:28][CH3:29])=[N:14]2)=[C:24]([CH3:25])[CH:23]=1

Participants

5

Reactant 3

HCID 18522661Acetone cardiceHCID 21225700DiisobutylaluminumhydrideHCID 539898611-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

Product 1

HCID 218373201-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl-methanolYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a dry ice/acetone bath-chilled solution of 1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester (1.1 g, 3.1 mmol) in anhydrous tetrahydrofuran (8 ml), diisobutylaluminum hydride (1.0 M in toluene; 10 ml, 10 mmol) was added dropwise. After 15 minutes, the reaction mixture was warmed to 0°-5° C. and stirred at that temperature for 2.5 hours. The reaction was then quenched by addition of 2 ml of water, and the organic solvent was removed in vacuo. Extraction of the residual mixture with ethyl acetate, anhydrous sodium sulfate drying of the resulting extract, and its concentration in vacuo afforded the title compound as a yellow oil (0.77 g).

Workup

  1. temperaturethe reaction mixture was warmed to 0°-5° C.
  2. customThe reaction was then quenched by addition of 2 ml of water
  3. customthe organic solvent was removed in vacuo
  4. extractionExtraction of the residual mixture with ethyl acetate, anhydrous sodium sulfate
  5. customdrying of the resulting
  6. extractionextract
  7. concentrationits concentration in vacuo

Sources & evidence

ORD record
ord-45aea6c38cb640fb8e048faf18b81a92
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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