Reaktionsgleichung
CO[CH:3](OC)[CH2:4][NH2:5].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.Cl>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:15]([CH:3]=[CH:4][N:5]=[CH:13]2)=[CH:16][CH:17]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 5 °C
Versuchsvorschrift
Aminoacetaldehyde dimethyl acetal (81.9 mL) was added to a solution of 60.8 mL of 3-methoxy-benzaldehyde in 600 mL of toluene. The mixture was refluxed for 5 h using a Dean-Stark trap and subsequently cooled to 5° C. In a nitrogene atmosphere trifluoroacetic acid anhydride (209 mL) and borontrifluoride etherate (185 mL) were added in succession at such a rate, that the internal temperature was kept below 10° C. After stirring for 3 days at room temperature the the reaction mixture was poured on ice, 250 mL 2 N hydrochloric acid added and the organic layer extracted with 1 N hydrochloric acid. The pH value of the combined aqueous extracts was adjusted to pH 9 by adding concentrated aqueous ammonia. Extraction with ethyl acetate, followed by drying and removal of the solvent in vacuo gave 66.9 g (84%) of the title compound as a light brownish oil. EI-MS: 159 (M+).
Aufarbeitung
- temperatureThe mixture was refluxed for 5 h
- customwas kept below 10° C
- additionadded
- extractionthe organic layer extracted with 1 N hydrochloric acid
- additionby adding concentrated aqueous ammonia
- extractionExtraction with ethyl acetate
- customby drying
- customremoval of the solvent in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-65a3908523a2442586c8153812403d65
- Quelldatensatz
- uspto-grants-2001_02
- Patentnummer
- US06194409B1
Verknüpfte Notizen
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