Water → 2-t-butyl-5-(p-fluorobenzyloxy)-4-methyl-3(2H)-pyridazinone

HRID 2352023Notes

Reaction equation

HRID 2352023 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:12]([N:16]1[C:21](=[O:22])[C:20]([CH3:23])=[C:19](Cl)[CH:18]=[N:17]1)([CH3:15])([CH3:14])[CH3:13].O>CN(C)C=O>[C:12]([N:16]1[C:21](=[O:22])[C:20]([CH3:23])=[C:19]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[CH:18]=[N:17]1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680224-Fluorobenzylic alcoholHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

Product 1

HCID 138251372-t-butyl-5-(p-fluorobenzyloxy)-4-methyl-3(2H)-pyridazinoneYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.63 g (0.005 mol) of p-fluorobenzyl alcohol dissolved in 20 ml of N,N-dimethylformamide was added 0.24 g of 55% sodium hydride at room temperature under stirring. After addition, the resulting mixture was further stirred at room temperature for fifteen minutes. The reaction liquid was added dropwise with 1.0 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone, and was stirred at room temperature for eight hours. The reaction mixture was poured into 200 ml of water and then extracted with 50 ml of benzene. The resulting benzene layer was washed successively with 50 ml of 10% sodium hydroxide, 50 ml of 1N-hydrochloric acid, and 100 ml of water, dried over anhydrous sodium sulfate, and freed of solvent by distillation to give 1.5 g of crude product. The crude product was recrystallized from 20 ml of hexane to obtain 0.9 g of 2-t-butyl-5-(p-fluorobenzyloxy)-4-methyl-3(2H)-pyridazinone.

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was further stirred at room temperature for fifteen minutes
  3. customThe reaction liquid
  4. stirringwas stirred at room temperature for eight hours
  5. extractionextracted with 50 ml of benzene
  6. washThe resulting benzene layer was washed successively with 50 ml of 10% sodium hydroxide, 50 ml of 1N-hydrochloric acid, and 100 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationfreed of solvent by distillation
  9. customto give 1.5 g of crude product
  10. customThe crude product was recrystallized from 20 ml of hexane

Sources & evidence

ORD record
ord-b8c5a5d0778049ce95bddad55a7a06ec
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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