Benzyl Alcohol → 3,4-bis(benzyloxy)-6-[(E)-2-(3,5-difluorophenyl)vinyl]pyridazine
Reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]1[CH:13]=[C:14](/[CH:19]=[CH:20]/[C:21]2[N:26]=[N:25][C:24]3O[C:28]4[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=4[O:30][C:23]=3[CH:22]=2)[CH:15]=[C:16]([F:18])[CH:17]=1.O.O1CCC[CH2:37]1>>[CH2:1]([O:8][C:24]1[N:25]=[N:26][C:21](/[CH:20]=[CH:19]/[C:14]2[CH:15]=[C:16]([F:18])[CH:17]=[C:12]([F:11])[CH:13]=2)=[CH:22][C:23]=1[O:30][CH2:29][C:31]1[CH:32]=[CH:33][CH:34]=[CH:28][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Procedure
Under ice-cooling, to a solution (20 mL) of benzyl alcohol (580 mg) in tetrahydrofuran was added 60% sodium hydride (220 mg), and the mixture was stirred for 10 min. To the mixture was added a solution (10 mL) of 3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine (700 mg) in tetrahydrofuran, and the mixture was stirred at 60° C. for 4 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was 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-(3,5-difluorophenyl)vinyl]pyridazine (710 mg).
Workup
- stirringthe mixture was stirred at 60° C. for 4 hr
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationthe solvent was concentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-abd0bef2b770471797fa55eee05f2d6d
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212147B2
Reaction notes
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