Benzyl Bromide → 5-(Benzyloxy)-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

HRID 564045

Reaktionsgleichung

Reaktionsgleichung von HRID 564045
[OH:1][C:2]1[CH:7]=[N:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[C:4](=[O:14])[CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.[OH-].[Na+]>[CH2:15]([O:1][C:2]1[CH:7]=[N:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[C:4](=[O:14])[CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 2

HCID 7498Benzyl BromideHCID 579503555-Hydroxy-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

Produkt 1

HCID 670073955-(Benzyloxy)-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To 500 mg (2.55 mmol) 5-hydroxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (preparation 5a) in THF is added at 0° C. subsequently 315 mg (2.80 mmol) potassium-tert-butylate, 47 mg (0.13 mmol) tetra-butylammonium-iodide and 0.45 mL (3.82 mmol) benzylbromide. The reaction mixture is stirred overnight at RT and is diluted with EtOAc and 1M aqueous sodium hydroxide solution. The organic phase is separated, washed with water and dried over MgSO4. After filtration, the solvent is evaporated and the residue is elutriated in tert-butylmethylether. The precipitate is collected and dried.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. customthe solvent is evaporated
  6. customThe precipitate is collected
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-531fed6b3cce4419918d2fe843f30512
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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