Diisopropyl Ether → HCID 13822293, compound

HRID 1904254Notes

Reaction equation

HRID 1904254 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:20]([N:24]1[C:29](=[O:30])[C:28]([Cl:31])=[C:27](Cl)[CH:26]=[N:25]1)([CH3:23])([CH3:22])[CH3:21].C(OC(C)C)(C)C>CN(C)C=O>[C:20]([N:24]1[C:29](=[O:30])[C:28]([Cl:31])=[C:27]([O:15][CH2:14][C:11]2[CH:12]=[N:13][C:8]([O:7][CH2:6][C:5]3[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[CH:26]=[N:25]1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 13822268HCID 13822268, compound

Product 1

HCID 13822293HCID 13822293, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.3 g of 6-(4-fluorobenzyloxy)-3-pyridine methanol in 20 ml of N,N-dimethylformamide was added under stirring at 0° C. 0.5 g of 55% sodium hydride (in mineral oil). After stirring for 30 minutes at room temperature, thereto was added 2.2 g of 2-t-butyl-4,5-dichloro-3(2H)-pyridazinone. The reaction mixture was stirred at room temperature for additional 8 hours, poured into 50 ml of ice water and extracted twice with 50 ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to give 4.1 g of a crude product. The crude product was added with isopropyl ether and recrystallized therefrom to obtain 3.2 g of 2-t-butyl-4-chloro-5-[{6-(4-fluorobenzyloxy)-3-pyridyl}-methyloxy]-3(2H)-pyridazinone, m.p. 121.0°~124.0° C.

Workup

  1. stirringAfter stirring for 30 minutes at room temperature
  2. stirringThe reaction mixture was stirred at room temperature for additional 8 hours
  3. extractionextracted twice with 50 ml of benzene
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfreed of solvent by distillation under reduced pressure
  7. customto give 4.1 g of a crude product
  8. customrecrystallized

Sources & evidence

ORD record
ord-4b0a322a33cc4f6fa3d391af9b01db13
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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