Реакция #5717

Уравнение реакции

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

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

Выход 112.8%

Растворители

cyclohexane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   Температураwhile cooling in an ice/water bath in such a manner that the temperature
4. 4
   Другоеremains between 20°-23°
5. 5
   ФильтрацияThe precipitate was filtered off
6. 6
   Промывкаthe filter cake was washed with cyclohexane
7. 7
   Экстракцияthe filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   СушкаThe organic phase was dried over magnesium sulphate
9. 9
   Фильтрацияfiltered
10. 10
    Промывкаthe filter cake was washed with cyclohexane
11. 11
    Другоеthe filtrates were evaporated

Методика

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.

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