Reaktion #5717

Reaktionsgleichung

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

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

Ausbeute 112.8%

Lösungsmittel

cyclohexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   Temperaturwhile cooling in an ice/water bath in such a manner that the temperature
4. 4
   Sonstigeremains between 20°-23°
5. 5
   FiltrationThe precipitate was filtered off
6. 6
   Waschenthe filter cake was washed with cyclohexane
7. 7
   Extraktionthe filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   TrocknenThe organic phase was dried over magnesium sulphate
9. 9
   Filtrationfiltered
10. 10
    Waschenthe filter cake was washed with cyclohexane
11. 11
    Sonstigethe filtrates were evaporated

Vorschrift

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.

Quelle