تفاعل #5717

معادلة التفاعل

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

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

المردود 112.8%

المذيبات

cyclohexane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   درجة الحرارةwhile cooling in an ice/water bath in such a manner that the temperature
4. 4
   أخرىremains between 20°-23°
5. 5
   ترشيحThe precipitate was filtered off
6. 6
   غسيلthe filter cake was washed with cyclohexane
7. 7
   استخلاصthe filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   تجفيفThe organic phase was dried over magnesium sulphate
9. 9
   ترشيحfiltered
10. 10
    غسيلthe filter cake was washed with cyclohexane
11. 11
    أخرىthe filtrates were evaporated

الإجراء التجريبي

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.

المصدر