反応 #5717

反応方程式

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

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

収率 112.8%

溶媒

cyclohexane

反応条件

後処理

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
   その他remains between 20°-23°
5. 5
   ろ過The precipitate was filtered off
6. 6
   洗浄the filter cake was washed with cyclohexane
7. 7
   抽出the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   乾燥The organic phase was dried over magnesium sulphate
9. 9
   ろ過filtered
10. 10
    洗浄the filter cake was washed with cyclohexane
11. 11
    その他the filtrates were evaporated

実験手順

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.

出典