Lithium Hydroxide → (1-Methyl-3-phenyl-1H-pyrazol-5-yl)methanol

HRID 1774553Notes

Reaction equation

HRID 1774553 reaction equation
C([O:9][CH2:10][C:11]#[C:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C1C=CC=CC=1.[CH3:21][NH:22][NH2:23].[OH-].[Li+]>C(O)C.O>[CH3:21][N:22]1[C:11]([CH2:10][OH:9])=[CH:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:23]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6061MethylhydrazineHCID 90092932HCID 90092932, compound

Product 1

HCID 7537632(1-Methyl-3-phenyl-1H-pyrazol-5-yl)methanolYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-oxo-4-phenylbut-2-yn-1-yl benzoate (1a) (750 mg, 2.84 mmol) and methylhydrazine (0.30 mL, 5.68 mmol) in ethanol (25 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was taken in a mixture of ethanol (3 mL) and tetrahydrofuran (9 mL). Lithium hydroxide (204 mg, 8.51 mmol), previously dissolved in water (3 mL) was added and the mixture was stirred at room temperature for 2 hours. Ethanol and tetrahydrofuran were removed under reduced pressure and the resulting aqueous layer was extracted with ethyl acetate (2×5 mL). The organic layer was successively washed with a saturated solution of sodium hydrogenocarbonate (5 mL) and brine (5 mL) before being dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 50/50) to provide (1-methyl-3-phenyl-1H-pyrazol-5-yl)methanol (1b) (341 mg, 1.81 mmol, 64%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was taken in a mixture of ethanol (3 mL) and tetrahydrofuran (9 mL)
  3. additionwas added
  4. customEthanol and tetrahydrofuran were removed under reduced pressure
  5. extractionthe resulting aqueous layer was extracted with ethyl acetate (2×5 mL)
  6. washThe organic layer was successively washed with a saturated solution of sodium hydrogenocarbonate (5 mL) and brine (5 mL)
  7. dry with materialbefore being dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 50/50)

Sources & evidence

ORD record
ord-dca625078b0e4566835d2b9405703b6c
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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