반응 #94491

반응 방정식

DL-cysteine ethyl ester hydrochloride

1-hexyne

2,2'-azobis-(2-methylpropionitrile)

→

(1-hexenyl) sulfide

용매

dioxane

반응 조건

후처리

1. 1
   온도After cooling, most of the solvent
2. 2
   기타was evaporated in vacuo
3. 3
   workup.ADDITIONThe residue was treated with 150 ml of 1N sodium carbonate solution
4. 4
   추출extracted three times with ethyl acetate
5. 5
   세척washed with 3 × 50 ml of saturated brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타evaporated in vacuo

실험 절차

A mixture of 12.80 g (68.93 mmol) of DL-cysteine ethyl ester hydrochloride, 25.60 g (311.62 mmol) of 1-hexyne, and 50 mg of 2,2'-azobis-(2-methylpropionitrile) in 250 ml of absolute dioxane was stirred at 60°-65°. under inert gas atmosphere for 20 minutes. After cooling, most of the solvent was evaporated in vacuo. The residue was treated with 150 ml of 1N sodium carbonate solution and extracted three times with ethyl acetate. The organic phases were combined, washed with 3 × 50 ml of saturated brine, dried over anhydrous sodium sulfate and evaporated in vacuo to give 15.90 g (99%) of crude (ethyl 2-aminopropanoate-3-yl) (1-hexenyl) sulfide as a thick pale yellow oil which can be used without further purification in the next step. NMR spectroscopical studies showed that the product is approximately a 1:1 mixture of geometrical isomers.

출처