Reaktion #446567

Reaktionsgleichung

sodium chloride

3-thiophenecarboxaldehyde

2,5-dimethyl-2-(4-fluorophenyl)-3(2H)-furanone

sodium hydroxide

→

solid

Ausbeute 62.0%

2-(4-Fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

Ausbeute 62.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with dichloromethane (3×100 mL)
2. 2
   WaschenThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give a brown oil
7. 7
   SonstigeThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

Vorschrift

To a solution of 3-thiophenecarboxaldehyde (1.3 g, 1.2 mM) and 2,5-dimethyl-2-(4-fluorophenyl)-3(2H)-furanone (2.0 g, 9.8 mM) in ethanol (75 mL), was added 1N aqueous sodium hydroxide (2 mL, 2 mM). The reaction solution was stirred at room temperature for one day. After 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 brown oil. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford a yellow solid (1.8 g, 62% yield), m.p. 97°-98° C.

Quelle