反应 #969855

反应方程式

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

收率 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

收率 65.0%

反应条件

后处理

1. 1
   其他room temperature overnight
2. 2
   浓缩The mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   洗涤washed with saturated NaHCO3
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他purified by SiO2 chromatography (1:4 EtAC/Hexane)

实验过程

(Z)-ethyl 3-cyanoacrylate (5.01 g, 40.00 mmol) in 80 ml of THF at −20° C. was added the solution of thiol acetic acid (5.0 ml, 70.15 mmol) and DIPEA (16.0 ml, 92.03 mmol) in 20 ml of THF in 30 min. The reaction was kept at −20° C. for 4 hr then room temperature overnight. The mixture was concentrated, diluted with CH2Cl2, washed with saturated NaHCO3, dried over MgSO4, filtered, evaporated and purified by SiO2 chromatography (1:4 EtAC/Hexane) to afford 5.22 g (65%) of the title compound. Rf=0.25 (1:4 EtAC/Hexane); 1H NMR (CDCl3), 4.44 (m, 1H), 4.11 (dd, 2H, J=7.1, 14.3 Hz), 3.38 (m, 1H), 3.15 (m, 1H), 2.17 (s, 3H), 1.19 (t, 3H, J=7.2 Hz); 13C NMR 194.12, 173.21, 119.82, 61.35, 33.52, 30.08, 14.62; MS m/z+ 225.9 (MW+Na), m/z− 201.7 (MW−H).

来源