반응 #44337

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Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

용매

dichloromethane

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후처리

1. 1
   기타The reaction was quenched with 35 mL water
2. 2
   기타to yield
3. 3
   기타to provide a clear solution
4. 4
   추출The solution was extracted with dichloromethane 2×25 mL
5. 5
   건조dried with Na2SO4
6. 6
   기타the solvent evaporated
7. 7
   기타to provide a yellow oil
8. 8
   추출after extraction

실험 절차

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.

출처