Réaction #636580

Équation de réaction

(E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester

3-butynyl p-toluenesulfonate

potassium carbonate

→

(E)-3-[4-(1-but-3-ynyl-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester

Rendement 63.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooled to room temperature
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   Concentrationconcentrated
4. 4
   Autrepurified via silica gel column chromatography
5. 5
   Autrethe residue was recrystallized from heptane

Mode opératoire

A mixture of (E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (5.52 g, 20.6 mmol), 3-butynyl p-toluenesulfonate (4.55 mL, 24.7 mmol) and potassium carbonate (5.98 g, 43.3 mmol) in acetonitrile (15 mL) was heated at 65° C. for 9 h. After cooled to room temperature, the reaction mixture was filtered, concentrated, and purified via silica gel column chromatography, and the residue was recrystallized from heptane to provide (E)-3-[4-(1-but-3-ynyl-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (3.68 g, 63% yield). LCMS (m/z): 284.2 (M+1).

Source