Reacción #44337

Ecuación de reacción

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with 35 mL water
2. 2
   Otroto yield
3. 3
   Otroto provide a clear solution
4. 4
   ExtracciónThe solution was extracted with dichloromethane 2×25 mL
5. 5
   Secadodried with Na2SO4
6. 6
   Otrothe solvent evaporated
7. 7
   Otroto provide a yellow oil
8. 8
   Extracciónafter extraction

Procedimiento

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.

Fuente