1-Phenyl-1H-pyrazole-3-carbaldehyde → 1-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-ol

HRID 2063546Notes

Reaction equation

HRID 2063546 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][CH2:15][Mg+].[Br-]>C1COCC1>[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([CH:12]([OH:13])[CH2:14][CH3:15])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 134324761-Phenyl-1H-pyrazole-3-carbaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 593661741-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-olYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Phenyl-1H-pyrazole-3-carbaldehyde (779 mg, 4.53 mmol) was dissolved in anhydrous THF (9 mL) and chilled in an ice bath. EtMgBr (3.0 M in Et2O, 4.5 mL) was added dropwise. After 1.5 hours, the reaction mixture was allowed to warm to ambient temperature. TLC (2:1 hexanes:EtOAc indicated complete consumption of aldehyde starting material. The reaction mixture was quenched with water and extracted with EtOAc (2×). The EtOAc layers were washed with brine (1×), dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (2:1 hexanes:EtOAc) to provide the title compound (631 mg, 69%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 1H, J=2.4 Hz), 7.65 (d, 2H, J=7.6 Hz), 7.42 (t, 2H, J=7.6 Hz), 7.27 (d, 1H, J=7.2 Hz), 6.38 (d, 1H, J=2.4 Hz), 4.79 (dd, 1H, J=12, 5.6 Hz), 2.38 (d, 1H, J=4.8 Hz), 1.98-1.81 (m, 2H), 1.01 (t, 3H, J=7.2 Hz). MS (ES) m/z 203.1 (M+H+).

Workup

  1. temperaturechilled in an ice bath
  2. customTLC (2:1 hexanes:EtOAc indicated complete consumption of aldehyde starting material
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc (2×)
  5. washThe EtOAc layers were washed with brine (1×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-b80ec1f6edf34b44a045ba4d752d313f
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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