反应 #160677

反应方程式

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

(3RS,4SR)-3-(3,4-Dimethoxyphenyl)-4-nitrocyclohexanone

溶剂

ethyl acetate

反应条件

后处理

1. 1
   温度cooled
2. 2
   workup.ADDITIONare dropped
3. 3
   workup.STIRRINGunder stirring
4. 4
   其他The phases are separated
5. 5
   萃取the aqueous layer is extracted three times with dichloromethane
6. 6
   洗涤The combined organic extracts are washed with saturated sodium hydrogencarbonate solution
7. 7
   干燥dried over magnesium sulfate
8. 8
   其他the solvents are removed under reduced pressure
9. 9
   其他to give 150 g of the crude title compound
10. 10
    其他Further purification

实验过程

90.0 g of 3,4-dimethoxy-ω-nitrostyrene (compound G2), 90 ml of 2-trimethylsilyloxy-1,3-butadiene and 180 ml of abs. Toluene are put in an autoclave, where the mixture is stirred at 140° C. for 2 days and then cooled. After addition of 1000 ml of ethyl acetate, 300 ml of a 2 N solution of hydrochloric acid are dropped under stirring. The phases are separated and the aqueous layer is extracted three times with dichloromethane. The combined organic extracts are washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and the solvents are removed under reduced pressure to give 150 g of the crude title compound. Further purification is carried out by chromatography on silica gel using petroleum ether/ethyl acetate in the ratio 1/1 as eluent to give 81.5 g (67% of theory) of the pure title compound.

来源