Reaktionsgleichung
[CH:1]([Mg]Br)=[CH2:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10]Br>C1COCC1.[Cu]I>[CH2:10]([C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=1)[CH:1]=[CH2:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a suspension of 308 mg (1.62 mmol, 25 mol %) of copper (I) iodide in 30 mL of THF was added dropwise vinylmagnesium bromide as a 1 M solution in THF at −50° C. After stirring for 10 min, a solution of 1.5 g (6.49 mmol) of 3,5-dimethoxybenzyl bromide in 8 mL of THF was added, and the resulting solution was stirred at −30° C. for 1 h and then was warmed to room temperature. The reaction mixture was quenched by the slow addition of 20 mL of water. After stirring for 5 min, the layers were separated and the aqueous layer was extracted twice with 20-mL portions of ethyl acetate. The combined organic fractions were dried (Na2SO4), filtered through a plug of silica gel (eluted with ethyl acetate) and concentrated in vacuo to afford 1.2 g (100%) of product as a yellow oil.
Aufarbeitung
- stirringthe resulting solution was stirred at −30° C. for 1 h
- customThe reaction mixture was quenched by the slow addition of 20 mL of water
- stirringAfter stirring for 5 min
- customthe layers were separated
- extractionthe aqueous layer was extracted twice with 20-mL portions of ethyl acetate
- dry with materialThe combined organic fractions were dried (Na2SO4)
- filtrationfiltered through a plug of silica gel (eluted with ethyl acetate)
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-a6d2ac31885a416292c6aaa5e7957f88
- Quelldatensatz
- uspto-grants-2015_10
- Patentnummer
- US09156836B2
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