Reaktion #40907

Reaktionsgleichung

ammonium chloride

ethylmagnesium bromide

toluene

7-bromoindole

→

titled compound

{1-[(7-bromo-1H-indol-3-yl)methyl]cyclopropyl}acetonitrile

Lösungsmittel

diethyl ether

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 2.5 hours
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   WaschenThe organic layer was washed with water and saturated saline
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigethe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20)

Vorschrift

To a toluene (12 mL) solution of 7-bromoindole (1.00 g), [1-bromomethyl)cyclopropyl]acetonitrile (444 mg) was added and a diethyl ether solution (1.7 mL) of 3M ethylmagnesium bromide was added dropwise under ice cooling, and then the mixture was refluxed for 2.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20) to obtain the titled compound having the following physical properties (390 mg).

Quelle