反应 #1880962
ord-3380c135880a4bff9e4e413aac9a1023
反应方程式
反应物
反应条件
后处理
- 1其他falling to 15° C
- 2workup.STIRRINGAfter stirring for 30 min
- 3workup.STIRRINGThe mixture was stirred for 48 h at room temperature, in the course of which, after 6 h
- 4萃取the product was extracted three times
- 5洗涤The combined organic extracts were washed with 200 ml of 20% sodium hydrogen sulfite solution and 200 ml of water
- 6干燥dried over sodium sulfate
- 7其他After removing the solvent
- 8其他on a rotary evaporator and flash chromatography (pentane/ether, 4:1, Rf=0.32) on silica gel
实验过程
6.6 g (30.5 mmol) of 1-methyl-7-methylene-2,3,7,8-tetrahydro-1H,6H-5,9-dioxacyclohepta[f]indene were dissolved in a mixture of 140 ml of acetonitrile, 140 ml of water and 90 ml of carbon tetrachloride. 6.50 g (30.5 mmol) of sodium periodate were added at room temperature with stirring, with the temperature falling to 15° C. After stirring for 30 min, 0.3 g (1.5 mmol, 5 mol %) of ruthenium (III) chloride hydrate were then added, with the temperature increasing back to 30° C. The mixture was stirred for 48 h at room temperature, in the course of which, after 6 h, a further 6.50 g (30.5 mmol) of sodium periodate and 0.3 g (1.5 mmol, 5 mol %) of ruthenium (III) chloride hydrate were added. The reaction mixture was then poured into 500 ml of water and the product was extracted three times, each time with 200 ml of dichloromethane. The combined organic extracts were washed with 200 ml of 20% sodium hydrogen sulfite solution and 200 ml of water and dried over sodium sulfate. After removing the solvent on a rotary evaporator and flash chromatography (pentane/ether, 4:1, Rf=0.32) on silica gel, 3.3 g (50%) of 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one (2) were obtained as colorless crystals of m.p. 79–80° C.