Reaktion #12060

Reaktionsgleichung

benzyl magnesium chloride

2-bromo-indene

→

2-benzylindene

Lösungsmittel

ether

diethyl ether

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux overnight
3. 3
   Sonstigequenched
4. 4
   workup.ADDITIONadding 150 mL of 1.0 M aqueous hydrochloric acid
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed twice with 50 mL of ether
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe volatiles removed in vacuo
10. 10
    Sonstigeto leave a dark oil
11. 11
    Sonstigepurified by flash column chromatography

Vorschrift

A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then quenched by cooling to 0° C. and adding 150 mL of 1.0 M aqueous hydrochloric acid. The organic layer was separated and washed twice with 50 mL of ether. The organic extracts were combined, dried over magnesium sulfate, filtered and the volatiles removed in vacuo to leave a dark oil. The sample was dissolved in a small amount of hexanes and purified by flash column chromatography using silica and hexanes as the elutent. Yield: 1.75 g, 66 percent

Quelle