反応 #44337

反応方程式

Vanillin

Vanillin

methyl isonipecotate

propargyl bromide

→

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他The reaction was quenched with 35 mL water
2. 2
   その他to yield
3. 3
   その他to provide a clear solution
4. 4
   抽出The solution was extracted with dichloromethane 2×25 mL
5. 5
   乾燥dried with Na2SO4
6. 6
   その他the solvent evaporated
7. 7
   その他to provide a yellow oil
8. 8
   抽出after extraction

実験手順

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.

出典