Water → HCID 13825147, compound

HRID 2352024Notes

Reaction equation

HRID 2352024 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([OH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][Si:15]([CH3:25])([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([O:13][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([Si:15]([CH3:14])([CH3:25])[CH3:24])=[CH:17][CH:18]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12583976HCID 12583976, compoundHCID 547131062-tert-Butyl-5-hydroxy-4-methylpyridazin-3(2H)-one

Product 1

HCID 13825147HCID 13825147, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.9 g (0.005 mol) of 2-t-butyl-5-hydroxy-4-methyl-3(2H)-pyridazinone and 1.2 g (0.005 mol) of p-trimethylsilyl benzylbromide dissolved in 20 ml of N,N-dimethylformamide was added 1.0 g (0.007 mol) of potassium carbonate at room temperature under stirring. After addition, the resulting mixture was stirred at 120° C. for three hours. After allowed to cool, the reaction mixture was poured into 200 ml of water and extracted with 100 ml of benzene. The resulting benzene layer was washed with 100 ml of water, dried over anhydrous sodium sulfate, and freed of solvent by distillation to give 1.8 g of crude product. The crude product was recrystallized from 20 ml of hexane to obtain 1.2 g of 2-t-butyl-4-methyl-5-(p-trimethylsilyl benzyloxy)-3(2H)-pyridazinone.

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was stirred at 120° C. for three hours
  3. temperatureto cool
  4. extractionextracted with 100 ml of benzene
  5. washThe resulting benzene layer was washed with 100 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationfreed of solvent by distillation
  8. customto give 1.8 g of crude product
  9. customThe crude product was recrystallized from 20 ml of hexane

Sources & evidence

ORD record
ord-256ff7dc361a4ff68863413698051125
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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