Reaction #44337

Reaction equation

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe reaction was quenched with 35 mL water
2. 2
   Otherto yield
3. 3
   Otherto provide a clear solution
4. 4
   ExtractionThe solution was extracted with dichloromethane 2×25 mL
5. 5
   Dryingdried with Na2SO4
6. 6
   Otherthe solvent evaporated
7. 7
   Otherto provide a yellow oil
8. 8
   Extractionafter extraction

Procedure

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.

Source