Pyridine → Methyl (E)-11-[2-(3-pyridyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[CH2:14]/[CH:15]=[C:16]1/[C:17]2[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[CH:28]=[CH:27][C:18]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]/1=2>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:14]/[CH:15]=[C:16]2/[C:17]3[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[CH:28]=[CH:27][C:18]=3[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]/2=3)[CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 50 ml of pyridine was added 2.0 g of lithium aluminum hydride, and the mixture was stirred at room temperature for one night. Then, 90 ml of tetrahydrofuran solution containing 5.0 g of Compound h was dropwise added thereto under ice-cooling. The mixture was stirred at room temperature for 5 hours, and the solvent was distilled off under reduced pressure. The residue was washed with tetrahydrofuran, and the washings were concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate:triethylamine=10:10:1) to give 1.7 g of the desired product.
Workup
- additionwas dropwise added
- temperatureunder ice-cooling
- stirringThe mixture was stirred at room temperature for 5 hours
- distillationthe solvent was distilled off under reduced pressure
- washThe residue was washed with tetrahydrofuran
- concentrationthe washings were concentrated under reduced pressure
- washThe residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate:triethylamine=10:10:1)
Sources & evidence
- ORD record
- ord-0050646498fe4646886f4884c628565e
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05302596
Reaction notes
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