반응 #5717

반응 방정식

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

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

수율 112.8%

용매

cyclohexane

반응 조건

후처리

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   온도while cooling in an ice/water bath in such a manner that the temperature
4. 4
   기타remains between 20°-23°
5. 5
   여과The precipitate was filtered off
6. 6
   세척the filter cake was washed with cyclohexane
7. 7
   추출the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   건조The organic phase was dried over magnesium sulphate
9. 9
   여과filtered
10. 10
    세척the filter cake was washed with cyclohexane
11. 11
    기타the filtrates were evaporated

실험 절차

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.

출처