反应 #5717

反应方程式

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

methyl (R)-3-(benzyloxy)-tetradecanoate

收率 112.8%

溶剂

cyclohexane

反应条件

后处理

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   温度while cooling in an ice/water bath in such a manner that the temperature
4. 4
   其他remains between 20°-23°
5. 5
   过滤The precipitate was filtered off
6. 6
   洗涤the filter cake was washed with cyclohexane
7. 7
   萃取the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   干燥The organic phase was dried over magnesium sulphate
9. 9
   过滤filtered
10. 10
    洗涤the filter cake was washed with cyclohexane
11. 11
    其他the filtrates were evaporated

实验过程

A suspension of 206.7 g of methyl (R)-3-hydroxytetradecanoate in 1000 ml of cyclohexane was treated under nitrogen and while stirring with 214.2 g of benzyl trichloroacetimidate and dissolved at 20°. 10 ml of trifluoromethanesulphonic acid were added dropwise while cooling in an ice/water bath in such a manner that the temperature remains between 20°-23°. The resulting suspension was stirred at 25°-30°. The precipitate was filtered off, the filter cake was washed with cyclohexane, the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution. The organic phase was dried over magnesium sulphate, filtered, the filter cake was washed with cyclohexane and the filtrates were evaporated. 314.5 g of methyl (R)-3-(benzyloxy)-tetradecanoate were obtained.

来源