반응 #2261642

반응 방정식

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

수율 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

수율 65.0%

반응 조건

후처리

1. 1
   기타room temperature overnight
2. 2
   농축The mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   세척washed with saturated NaHCO3
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타purified by SiO2 chromatography (1:4 EtAC/Hexane)

실험 절차

(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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