Reaktionsgleichung
[CH3:1][CH:2]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].O>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([O:4][C:3](=[O:5])[CH:2]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:1])[CH:23]=[CH2:22]Komponenten
7
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 2-methylindol-4-yloxyacetic acid (2 g) in N,N-dimethylformamide (20 ml) was added anhydrous potassium carbonate (2.02 g) and allyl bromide (1.27 ml), and the mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added water and ethyl acetate, then separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane—ethyl acetate) to give the title compound (1.88 g) having the following physical data.
Aufarbeitung
- customseparated
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe combined organic layer was washed with water
- dry with materiala saturated aqueous solution of sodium chloride, successively, dried
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (n-hexane—ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-4de34738eb794861b9dd2d1ca54ec74b
- Quelldatensatz
- uspto-grants-2004_06
- Patentnummer
- US06743793B2
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