Reaktion #2001629

Reaktionsgleichung

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

Ausbeute 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

Ausbeute 65.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeroom temperature overnight
2. 2
   EinengenThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   Waschenwashed with saturated NaHCO3
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   Sonstigepurified by SiO2 chromatography (1:4 EtAC/Hexane)

Vorschrift

(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).

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