Benzene → Ethyl (3-methoxycarbonyl-6,11-dihydrodibenz[b,e]oxepin-11-yl)cyanoacetate
Reaction equation
CO[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:4]1=2.[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23].C(N(C(C)C)CC)(C)C.C1C=CC=CC=1>C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl.CO>[CH3:21][O:20][C:18]([C:15]1[CH:16]=[CH:17][C:4]2[CH:3]([CH:24]([C:22]#[N:23])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH2:7][O:6][C:5]=2[CH:14]=1)=[O:19]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Titanium tetrachloride (2.3 ml) was added to a mixture of 4.95 g of methyl 11-methoxy-6,11-dihydrodibenz[b,e]oxepin-3-carboxylate, 2.8 ml of ethyl cyanoacetate, 4.6 ml of diisopropylethylamine and 400 ml of benzene under ice cooling, and the mixture was stirred at room temperature for 2 days. Methanol (5 ml) was added thereto, and the mixture was diluted with ethyl acetate. The solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (3/1)] to give 0.72 g (11%) of the product.
Workup
- washThe solution was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (3/1)]
Sources & evidence
- ORD record
- ord-7a4d74731c234ead87cad7c4694bcd9b
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05478840
Reaction notes
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