反応 #446565

反応方程式

sodium chloride

p-cyanobenzaldehyde

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

sodium hydroxide

→

solid

収率 38.7%

4-[2-[2,3-Dihydro-2-(4-fluorophenyl)-2-methyl-3-oxo-5-furanyl]ethenyl]benzonitrile

収率 38.7%

溶媒

ethanol

反応条件

後処理

1. 1
   抽出The aqueous layer was extracted with dichloromethane (3×100 mL)
2. 2
   洗浄The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他to give an orange liquid
7. 7
   その他The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

実験手順

To a solution of p-cyanobenzaldehyde (1.6 g, 11.8 mM) and 2,5-dimethyl-2-(4-fluorphenyl)-3(2H)-furanone (2.0 g, 9.8 mM) in ethanol (75 mL), was added 1N aqueous sodium hydroxide (1.0 mL, 1 mM). After the reaction solution was stirred at room temperature for two days, 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 an orange liquid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to give a yellow crystalline solid (1.2 g, 38% yield), m.p. 140°-142° C.

出典