Reaktionsgleichung
[PH4+].[CH:2]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)=O.[CH2:15]1[O:19][CH2:18][CH2:17][CH2:16]1>>[O:19]1[C:18]2[CH:2]=[C:4](/[C:14](/[CH3:13])=[CH:2]/[C:4]3[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=3)[CH:5]=[CH:16][C:17]=2[CH2:8][CH2:7][CH2:6][CH2:15]1Komponenten
Versuchsvorschrift
4.9 g of 2,3,4,5-tetrahydro-α-methyl-1-benzoxepine-8-methanol were dissolved in 50 ml of acetonitrile and treated with 13 g of triphenylphosphine hydrobromide. The reaction mixture was stirred at 40° C. for 24 hours. Thereafter, the majority of the solvent was removed under reduced pressure and the residue was partitioned between hexane and ethanol/water (8:2). The heavy phase was evaporated and dried, whereby 11.96 g of white phosphonium salt were obtained. 6.29 g of Phosphonium salt were dissolved in 13 ml of butylene oxide, treated with 2.6 g of ethyl 4-formylbenzoate and heated to reflux for 18 hours. Thereafter, the majority of the solvent was removed under reduced pressure and the residue was partitioned between hexane and ethanol/water (8:2). The light phase was dried over magnesium sulfate and evaporated. Chromatography on silica gel (petroleum ether/ethyl acetate (97:3)) and recrystallization from hexane yielded 1.4 g of ethyl p-[(E)-2-(2,3,4,5-tetrahydro-1-benzoxepin-8-yl)propenyl]benzoate, m.p. 71°-72° C.
Aufarbeitung
- temperatureheated
- temperatureto reflux for 18 hours
- customThereafter, the majority of the solvent was removed under reduced pressure
- customthe residue was partitioned between hexane and ethanol/water (8:2)
- dry with materialThe light phase was dried over magnesium sulfate
- customevaporated
- customChromatography on silica gel (petroleum ether/ethyl acetate (97:3)) and recrystallization from hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-6c7edd5c9e5a47cb80feb5159bd26e11
- Quelldatensatz
- uspto-grants-1992_11
- Patentnummer
- US05164387
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