反応 #12060

反応方程式

benzyl magnesium chloride

2-bromo-indene

→

2-benzylindene

溶媒

ether

diethyl ether

—

hexanes

反応条件

後処理

1. 1
   温度The reaction was heated
2. 2
   温度to reflux overnight
3. 3
   その他quenched
4. 4
   workup.ADDITIONadding 150 mL of 1.0 M aqueous hydrochloric acid
5. 5
   その他The organic layer was separated
6. 6
   洗浄washed twice with 50 mL of ether
7. 7
   乾燥dried over magnesium sulfate
8. 8
   ろ過filtered
9. 9
   その他the volatiles removed in vacuo
10. 10
    その他to leave a dark oil
11. 11
    その他purified by flash column chromatography

実験手順

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

出典