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

HRID 564045Notes

Reaction equation

HRID 564045 reaction equation
[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-531fed6b3cce4419918d2fe843f30512
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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