反应 #452453

反应方程式

6-bromohexanoyl chloride

benzyl alcohol

→

Benzyl 6-bromohexanoate

溶剂

methylene chloride

pyridine

反应条件

后处理

1. 1
   温度The mixture was cooled
2. 2
   其他for 90 min
3. 3
   萃取The solution was extracted with 200 mL of 1 N HCl
4. 4
   干燥the solution dried over Na2SO4
5. 5
   过滤The solution was filtered
6. 6
   其他the solvent removed in vacuo
7. 7
   其他to give an oil
8. 8
   其他This oil was purified on silica gel
9. 9
   洗涤eluting with a gradient of chloroform in hexanes
10. 10
    workup.ADDITIONFractions containing the product (TLC Rf 0.52, CHCl3 /hexanes 6:4)
11. 11
    其他the solvent removed
12. 12
    其他to give 24.4 g

实验过程

Benzyl 6-bromohexanoate was prepared by dropwise addition of a solution of 6-bromohexanoyl chloride (20.0 mL) in 100 mL of methylene chloride to a solution of 66.22 mL of benzyl alcohol in 60 mL of pyridine. The mixture was cooled using an ice-water bath for 90 min, then stirred at room temperature for 18 h. The solution was extracted with 200 mL of 1 N HCl followed by 2×150 mL of sat. NaHCO3. The extracts were discarded and the solution dried over Na2SO4. The solution was filtered and the solvent removed in vacuo to give an oil. This oil was purified on silica gel, eluting with a gradient of chloroform in hexanes. Fractions containing the product (TLC Rf 0.52, CHCl3 /hexanes 6:4) were combined and the solvent removed to give 24.4 g.

来源