4-Methylmorpholine → (Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

Reaktionsgleichung

[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[C:12]([O:16][C:17](=[O:20])[C:18]#[CH:19])([CH3:15])([CH3:14])[CH3:13].CN1CCOCC1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]/[CH:19]=[CH:18]\[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[CH:7][CH:6]=1

Komponenten

Versuchsvorschrift

a mixture of 4-(2-methoxy ethyl)phenol (1.547 g, 10.3 mmol), propiolic acid tert-butyl ester (1.367 g, 10.8 mmol) and N-methyl morpholine (1.18 mL, 10.8 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 24 hours. The mixture was absorbed on SiO2 (20 g) and purified by column chromatography using a mixture of methylene chloride/hexane. The product was obtained as a two to one mixture of (E)/(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate isomers (2.0 g).