HCID 14497520, compound → 1-(4-Methoxyphenyl)-1H-pyrazole

HRID 1761566Notes

Reaction equation

HRID 1761566 reaction equation
C[Mg]Br.ClC1C=CC([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13](CCC=O)[CH:12]=2)=CC=1>CCOCC>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([N:15]2[CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14497520HCID 14497520, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleYield 162.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methyl magnesium bromide (MeMgBr) (2.20 ml, 7.04 mM) in Et2O (15 ml) at 0° C. was added a solution of the aldehyde 11 (1.60 g, 4.69 mM) in Et2O (70 ml) dropwise over a 30 minute period. After stirring for 1 hour the reaction was quenched with a saturated, aqueous NH4Cl solution. The reaction mixture was partitioned between EtOAc and H2O. The EtOAc solution was dried (MgSO4), filtered, and concentrated in vacuo. Chromatography (65 g, Baker 40 gm silica gel) of the residue with Et2O as eluent afforded 20 (1.33 g, 79%) as a clear light yellow oil.

Workup

  1. customwas quenched with a saturated, aqueous NH4Cl solution
  2. customThe reaction mixture was partitioned between EtOAc and H2O
  3. dry with materialThe EtOAc solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2362bfefbb4849c6a89f7b9a5f0f6f0f
Source dataset
uspto-grants-1989_05
Patent number
US04826868

Reaction notes

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