Reaktionsgleichung
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([CH2:11][CH:12]=O)=[CH:8][CH:7]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCCC1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[O:10][C:9]([CH2:11][CH2:12][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Next, the resulting (5-[1,3]dioxolan-2-yl-furan-2-yl)-acetaldehyde (1.57 g), aniline (0.94 mL, 10.3 mmol) and triacetoxy sodium borohydride (3.76 g, 17.2 mmol) were suspended in a mixture solution of tetrahydrofuran (30 mL) and acetic acid (1 mL) at 0° C., and the mixture was stirred at room temperature for 19 hours. An aqueous solution of saturated sodium bicarbonate was added to the reaction mixture at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (453 mg, 1.75 mmol, 14%) was obtained as a brown oil.
Aufarbeitung
- extractionwhich was then extracted with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated in vacuo
- customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-0d36fcdfba4d49b39c8d934b1b8c857c
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07932272B2
Verknüpfte Notizen
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