Benzyl Alcohol → 3,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine

HRID 1503204Notes

Reaction equation

HRID 1503204 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[K])(C)(C)C.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C)C=O.[C:27]1(/[CH:33]=[CH:34]/[C:35]2[N:40]=[N:39][C:38]3OC4C=CC=CC=4[O:44][C:37]=3[CH:36]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.O>[CH2:1]([O:8][C:38]1[N:39]=[N:40][C:35](/[CH:34]=[CH:33]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:36][C:37]=1[O:44][CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 21735183Dimethylformamide tolueneHCID 1176908813-[(E)-2-phenylvinyl][1,4]benzodioxino[2,3-c]pyridazineHCID 178418922HCID 178418922, compound

Product 1

HCID 1176911273,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Under ice-cooling, to a solution (5 mL) of benzyl alcohol (350 μL) in toluene was added t-butoxy potassium (375 mg), and the mixture was stirred for 20 min. To the mixture was added a toluene-dimethylformamide (1:1) suspension (10 ml) of 3-[(E)-2-phenylvinyl][1,4]benzodioxino[2,3-c]pyridazine (386 mg) at 0° C., and the mixture was stirred at 120° C. for 19 hr. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine (473 mg).

Workup

  1. stirringthe mixture was stirred at 120° C. for 19 hr
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0febadc63b7a499f97434a3b07967664
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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