Reacción #969855

Ecuación de reacción

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

Rendimiento 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

Rendimiento 65.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroroom temperature overnight
2. 2
   ConcentraciónThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   Lavadowashed with saturated NaHCO3
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   Otropurified by SiO2 chromatography (1:4 EtAC/Hexane)

Procedimiento

(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).

Fuente