Реакция #44337

Уравнение реакции

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

1-Prop-2-ynyl-piperidine-4-carboxylic acid methyl ester

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched with 35 mL water
2. 2
   Другоеto yield
3. 3
   Другоеto provide a clear solution
4. 4
   ЭкстракцияThe solution was extracted with dichloromethane 2×25 mL
5. 5
   Сушкаdried with Na2SO4
6. 6
   Другоеthe solvent evaporated
7. 7
   Другоеto provide a yellow oil
8. 8
   Экстракцияafter extraction

Методика

To a solution of methyl isonipecotate 3.5 g (24.4 mmol, 3.30 mL) in 100 mL dichloromethane was added TEA (1.5 eq, 36.6 mmol, 5.1 mL), propargyl bromide (3.0 eq, 73.2 mmol, 6.5 ml), at room temperature for 36 hrs. The reaction was quenched with 35 mL water to yield to provide a clear solution. The solution was extracted with dichloromethane 2×25 mL, dried with Na2SO4, and the solvent evaporated to provide a yellow oil. r.f. (40% EtOAc/Hexanes) 0.26 stains faint white with Vanillin, starting material r.f. 0.05 stains yellow with Vanillin. The product appeared pure after extraction.

Источник