Reaktion #446563

Reaktionsgleichung

sodium chloride

2-pyridinecarboxaldehyde

2,5-dimethyl-2-phenyl-3(2H)-furanone

undec-7ene

→

solid

Ausbeute 40.0%

2-Methyl-2-phenyl-5-[2-(2-pyridinyl)ethenyl]-3(2H)-furanone

Ausbeute 40.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter the reaction solution cooled to room temperature
2. 2
   ExtraktionThe aqueous layer was extracted with dichloromethane (3×100 mL)
3. 3
   WaschenThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give a yellow solid
8. 8
   SonstigePurification by trituration with 10% diethyl ether in hexane

Vorschrift

To a solution of 2-pyridinecarboxaldehyde (1.2 mL, 1.2 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (1.5 g, 8 mM) in ethanol (15 mL), was added 1,8-diazebicyclo[4.5.0]undec-7ene (DBU, 0.2 mL, 1.3 mM). The reaction solution was heated at 80° C. for 5 hours. After the reaction solution cooled to room temperature, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with dichloromethane (3×100 mL). The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a yellow solid. Purification by trituration with 10% diethyl ether in hexane gave a pale pink solid (887 mg, 40% yield), m.p. 74.5°-76° C.

Quelle