Reaction #969855

Reaction equation

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

Yield 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

Yield 65.0%

Conditions

Workup

1. 1
   Otherroom temperature overnight
2. 2
   ConcentrationThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   Washwashed with saturated NaHCO3
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   Otherpurified by SiO2 chromatography (1:4 EtAC/Hexane)

Procedure

(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