Sodium hydride → HCID 15390573, compound

HRID 1418708Notes

Reaction equation

HRID 1418708 reaction equation
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[N:4]1.C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)(=O)=O)=CC=1>CN(C)C=O>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH2:27][CH2:26][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1334121-(4-Hydroxybenzyl)pyrazoleHCID 14480093HCID 14480093, compound

Product 1

HCID 15390573HCID 15390573, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 10 ml of anhydrous N,N-dimethylformamide and 72 mg of sodium hydride (60% oil dispersion) was added dropwise an anhydrous N,N-dimethyl-formamide (5 ml) solution of 300 mg of 4-(1-pyrazolyl)methylphenol under stirring over 10 minutes. After stirring at room temperature for 1 hour, the mixture was cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (5 ml) solution of 505 mg of 2-(2-pyridyloxy)ethyl p-toluenesulfonate was added dropwise over 30 minutes. The mixture was stirred at room temperature overnight and then at 60° to 70° C. for further 2 hours. The reaction mixture was poured into 50 ml of ice water, which was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 208 mg of 4-(1-pyrazolyl)methylphenyl 2-(2-pyridyloxy)ethyl ether (compound 1). Yield, 41%.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. additionwas added dropwise over 30 minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. waitat 60° to 70° C. for further 2 hours
  5. extractionwas extracted twice with 30 ml of ethyl acetate
  6. washwashed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f8b5d72802b41feb5e8734b44eb6f9c
Source dataset
uspto-grants-1999_03
Patent number
US05883262

Reaction notes

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