تفاعل #160677

معادلة التفاعل

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

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

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   workup.ADDITIONare dropped
3. 3
   workup.STIRRINGunder stirring
4. 4
   أخرىThe phases are separated
5. 5
   استخلاصthe aqueous layer is extracted three times with dichloromethane
6. 6
   غسيلThe combined organic extracts are washed with saturated sodium hydrogencarbonate solution
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   أخرىthe solvents are removed under reduced pressure
9. 9
   أخرىto give 150 g of the crude title compound
10. 10
    أخرىFurther purification

الإجراء التجريبي

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.

المصدر