반응 #55973

반응 방정식

2-acetylthiophene

diethyl-o-cyanobenzylphosphonate

sodium methylate

→

2-[2-(2-thienyl)-1-propenyl]benzonitrile

용매

dimethyl formamide

dimethyl formamide

—

ice water

반응 조건

후처리

1. 1
   기타The starting material may be produced
2. 2
   workup.WAITat 100° for a further 2 hours
3. 3
   추출The condensation product is extracted with ether
4. 4
   세척the extract is washed with water until neutral,
5. 5
   건조is dried over potassium carbonate
6. 6
   농축concentrated by evaporation
7. 7
   기타The evaporation residue is chromatographed through 110 g of silica gel with a mixture of benzene/petroleum ether (1:4)

실험 절차

The starting material may be produced as follows: (a) A solution of 10.0 g of 2-acetylthiophene and 21.0 g of diethyl-o-cyanobenzylphosphonate in 70 cc of anhydrous dimethyl formamide is added dropwise at 20°-30° in an atmosphere of nitrogen to a suspension of 4.5 g of pulverized sodium methylate in 100 cc of anhydrous dimethyl formamide, the reaction mixture is stirred at 40° for 2 hours, and at 100° for a further 2 hours, is cooled to room temperature and diluted with 600 cc of ice water. The condensation product is extracted with ether, the extract is washed with water until neutral, is dried over potassium carbonate and concentrated by evaporation. The evaporation residue is chromatographed through 110 g of silica gel with a mixture of benzene/petroleum ether (1:4). The 2-[2-(2-thienyl)-1-propenyl]benzonitrile (nD20 =1.6460, B.P. 165°-175°/0.1 mm Hg), isolated as main fraction, is used for the next reaction without further purification.

출처