反应 #1880961

反应方程式

potassium carbonate

1-methylindane-5,6-diol

3-chloro-2-chloromethylprop-1-ene

→

1-methyl-7-methylene-2,3,7,8-tetrahydro-1H,6H-5,9-dioxacyclohepta[f]indene

收率 36.4%

溶剂

dioxane

反应条件

后处理

1. 1
   温度were heated
2. 2
   温度to reflux
3. 3
   workup.ADDITIONwas added dropwise
4. 4
   workup.ADDITIONWhen addition
5. 5
   workup.STIRRINGthe mixture was stirred for a further 1 h
6. 6
   温度under reflux
7. 7
   其他the inorganic solids precipitated out
8. 8
   过滤were filtered off with suction
9. 9
   温度after cooling the reaction mixture
10. 10
    洗涤The solids were washed with acetone
11. 11
    其他the combined organic phases freed from solvent on a rotary evaporator

实验过程

A suspension of 25.7 g (186 mmol) of potassium carbonate were heated to reflux with stirring. At this temperature, over the course of 5 h, a mixture of 15.3 g (93.2 mmol) of 1-methylindane-5,6-diol and 11.6 g (92.8 mmol) of 3-chloro-2-chloromethylprop-1-ene dissolved in 50 ml of dioxane was added dropwise. When addition was complete, the mixture was stirred for a further 1 h under reflux and the inorganic solids precipitated out were filtered off with suction after cooling the reaction mixture. The solids were washed with acetone and the combined organic phases freed from solvent on a rotary evaporator. After flash chromatography (pentane/ether, 19:1, Rf=0.66) on silica gel, 7.3 g (36%) of 1-methyl-7-methylene-2,3,7,8-tetrahydro-1H,6H-5,9-dioxacyclohepta[f]indene were obtained.

来源