반응 #12060

반응 방정식

benzyl magnesium chloride

2-bromo-indene

→

2-benzylindene

용매

ether

diethyl ether

—

hexanes

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도to reflux overnight
3. 3
   기타quenched
4. 4
   workup.ADDITIONadding 150 mL of 1.0 M aqueous hydrochloric acid
5. 5
   기타The organic layer was separated
6. 6
   세척washed twice with 50 mL of ether
7. 7
   건조dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   기타the volatiles removed in vacuo
10. 10
    기타to leave a dark oil
11. 11
    기타purified by flash column chromatography

실험 절차

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

출처