Réaction #969855

Équation de réaction

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

Rendement 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

Rendement 65.0%

Conditions de réaction

Traitement

1. 1
   Autreroom temperature overnight
2. 2
   ConcentrationThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   Lavagewashed with saturated NaHCO3
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   Autrepurified by SiO2 chromatography (1:4 EtAC/Hexane)

Mode opératoire

(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).

Source