反応 #452824

反応方程式

5-bromopent-1-ene

methyl 4-bromobenzoate

→

crude title compound

methyl 4-pent-4-enyl-benzoate

溶媒

THF

反応条件

後処理

1. 1
   温度The mixture was cooled to room temperature
2. 2
   その他The mixture was quenched with 3N HCl (aqueous)
3. 3
   抽出extracted with ethyl acetate
4. 4
   乾燥The combined organic extracts were dried over anhydrous MgSO4
5. 5
   その他evaporated at reduced pressure
6. 6
   その他The residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane)

実験手順

A mixture of dry Mg (900 mg, 37 mmol) and ZnBr2 (5.63 g, 25 mmol) in THF (25 mL) was treated with 5-bromopent-1-ene (4.45 mL, 37.6 mmol) and the subsequent suspension was heated at 56° C. for 18 h. The mixture was cooled to room temperature and methyl 4-bromobenzoate (7.1 g, 33 mmol) and tetrakis-(triphenylphosphine)palladium(0) (1.0 g, 0.865 mmol) were added, and the mixture was stirred at room temperature for 24 h. The mixture was quenched with 3N HCl (aqueous) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous MgSO4 and evaporated at reduced pressure. The residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane) to give the crude title compound which was used without further purification.

出典