Dimethylformamide → {4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol

HRID 507950Notes

Reaction equation

HRID 507950 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:17][C:18]2[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 178440651HCID 178440651, compound

Product 1

HCID 23157326{4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanolYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-tert-butyl-5-phenyl-1H-pyrazole (2.0 g, 10 mmol), 4-(chloromethyl)benzyl alcohol (1.70 g, 10.8 mmol), potassium carbonate (2.76 g, 20 mmol) and N,N-dimethylformamide (20 mL) was stirred at 120° C. for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (5%-80% ethyl acetate/hexane) to give the title compound (640 mg, yield 20%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (5%-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-544dfbc6bebf45f0b8c56d2f0b874118
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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