Reaktionsgleichung
[C:1](/[CH:3]=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2].[S:10]1C=CC=C1CC(O)=O.CCN(C(C)C)C(C)C.C1C[O:31][CH2:30][CH2:29]1>>[C:30]([S:10][CH:3]([C:1]#[N:2])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:31])[CH3:29]Komponenten
Versuchsvorschrift
(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).
Aufarbeitung
- customroom temperature overnight
- concentrationThe mixture was concentrated
- additiondiluted with CH2Cl2
- washwashed with saturated NaHCO3
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- custompurified by SiO2 chromatography (1:4 EtAC/Hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-ba6cdf2b3bb44480aa7b805b882d90d0
- Quelldatensatz
- uspto-grants-2012_08
- Patentnummer
- US08236319B2
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