Reaktionsgleichung
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5](OC)[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH3:2].[CH:20]([Li])([CH3:22])[CH3:21]>C1COCC1.CCCCC>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:20]([CH3:22])[CH3:21])[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
To a solution of 0.8 g (3.1 mmol) (E)-[1-(2-ethyl-6-methoxy-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine (Example 3 a)) in 3 ml dry THF cooled to −20° C. were added 9.62 ml of a 0.7M solution of isopropyl lithium in pentane drop-wise to keep temperature below 0° C. Then the mixture was stirred at −20° C. for further 30 min and the reaction quenched by addition of water. The aqueous phase was extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the crude product by flash chromatography on silica gel with heptane as eluent provided 0.220 g (E)-[1-(2-ethyl-6-isopropyl-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine as colourless liquid: MS (ISP): 274.1 (M+H+.).
Aufarbeitung
- customtemperature below 0° C
- customthe reaction quenched by addition of water
- extractionThe aqueous phase was extracted with ethyl acetate
- washthe combined extracts washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
- customPurification of the crude product by flash chromatography on silica gel with heptane as eluent
Quellen und Nachweise
- ORD-Eintrag
- ord-ed9b73ce17e54dcf999f7d6a2162a513
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07875645B2
Verknüpfte Notizen
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