Реакция #446315

Уравнение реакции

Water

Butyllithium

1,2,3,4-tetra -hydro-9-acridinamine

octyl chloroformate

→

octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate

Выход 56.3%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеat 0° C
2. 2
   Другоеthe cooling bath removed
3. 3
   workup.STIRRINGthe solution stirred over the weekend
4. 4
   Экстракцияthe mixture extracted with ethyl acetate
5. 5
   ДругоеThe ethyl acetate layer is separated
6. 6
   Другоеevaporated
7. 7
   Другоеto afford a yellow oil
8. 8
   ПромывкаChromatography (elution with isopropanol-chloroform (5:95))

Методика

n Butyllithium, 0.033 mol, is added to a suspension of 6.5g (0.033 mol) of 1,2,3,4-tetra -hydro-9-acridinamine (Petrow, V., Journal of the Chemical Society, pages 634 to 637 (1947)) in 200 ml of tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for 20 minutes, the cooling bath removed and 6.36 g (0.033 mol) of octyl chloroformate added and the solution stirred over the weekend. Water, 200 ml, is added and the mixture extracted with ethyl acetate. The ethyl acetate layer is separated and evaporated to afford a yellow oil. Chromatography (elution with isopropanol-chloroform (5:95)) affords 6.59 g of octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate, as a yelIow solid; mp 96-99° C.

Источник