反応 #969855

反応方程式

(Z)-ethyl 3-cyanoacrylate

thiol acetic acid

DIPEA

THF

THF

→

title compound

収率 65.0%

Ethyl 3-(acetylthio)-3-cyanopropanoate

収率 65.0%

反応条件

後処理

1. 1
   その他room temperature overnight
2. 2
   濃縮The mixture was concentrated
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   洗浄washed with saturated NaHCO3
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他purified by SiO2 chromatography (1:4 EtAC/Hexane)

実験手順

(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).

出典