Tetrahydrofuran → Methyl 11-methylene-6,11-dihydrodibenz-[b,e]oxepin-2-carboxylate
Reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2.O1CCC[CH2:22]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:22]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2Participants
4
Procedure
In 100 ml of tetrahydrofuran is suspended 25 g of methyltriphenylphosphonium bromide and 40 ml of 1.6 N-n-butyl lithium helium hexane solution is dropwise added thereto under a nitrogen atmosphere and ice-cooling. After stirring the mixture under ice-cooling for 30 minutes, a solution obtained by dissolving 15 g of methyl 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 250 ml of tetrahydrofuran is dropwise added thereto and the mixture is stirred at room temperature for two hours. The solvent is distilled away under reduced pressure and the residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1) to obtain 3.7 g of the desired product as a colorless oily matter.
Workup
- additionis dropwise added
- temperatureunder a nitrogen atmosphere and ice-cooling
- temperaturecooling for 30 minutes
- customa solution obtained
- additionis dropwise added
- stirringthe mixture is stirred at room temperature for two hours
- distillationThe solvent is distilled away under reduced pressure
- customthe residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-688a02543e90449cb79ab61337b3b473
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116863
Reaction notes
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