Reaktion #550238

Reaktionsgleichung

Methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate

pyridine

sodium hydrogencarbonate

→

methyl (E)-2-(1-methylethenyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate

Ausbeute 83.7%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThionyl chloirde (0.15 ml) was added to the solution
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionthe product was extracted with ethyl acetate
4. 4
   Sonstigethe crude product was chromatographed on silica gel
5. 5
   Waschenfollowed by elution with isopropyl ether:ethyl acetate (1:1)

Vorschrift

Methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate (0.3 g, 0.89 mmole) was dissolved in dichloromethane (10 ml), and the solution was cooled at -10° C. Thionyl chloirde (0.15 ml) was added to the solution, followed by adding pyridine (0.4 ml) and stirring for 10 minutes under the same reaction conditions. After the completion of the reaction, aqueous sodium hydrogencarbonate (5 ml) was added, and the product was extracted with ethyl acetate. The organic layer was worked up in the usual procedure, and the crude product was chromatographed on silica gel, followed by elution with isopropyl ether:ethyl acetate (1:1) to yield methyl (E)-2-(1-methylethenyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate (5-e) (0.25 g, 70%).

Quelle