Reaktion #44337

Reaktionsgleichung

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 35 mL water
2. 2
   Sonstigeto yield
3. 3
   Sonstigeto provide a clear solution
4. 4
   ExtraktionThe solution was extracted with dichloromethane 2×25 mL
5. 5
   Trocknendried with Na2SO4
6. 6
   Sonstigethe solvent evaporated
7. 7
   Sonstigeto provide a yellow oil
8. 8
   Extraktionafter extraction

Vorschrift

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.

Quelle