تفاعل #1755472

معادلة التفاعل

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with 35 mL water
2. 2
   أخرىto yield
3. 3
   أخرىto provide a clear solution
4. 4
   استخلاصThe solution was extracted with dichloromethane 2×25 mL
5. 5
   تجفيفdried with Na2SO4
6. 6
   أخرىthe solvent evaporated
7. 7
   أخرىto provide a yellow oil
8. 8
   استخلاصafter extraction

الإجراء التجريبي

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.

المصدر