Réaction #160677

Équation de réaction

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

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

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   workup.ADDITIONare dropped
3. 3
   workup.STIRRINGunder stirring
4. 4
   AutreThe phases are separated
5. 5
   Extractionthe aqueous layer is extracted three times with dichloromethane
6. 6
   LavageThe combined organic extracts are washed with saturated sodium hydrogencarbonate solution
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Autrethe solvents are removed under reduced pressure
9. 9
   Autreto give 150 g of the crude title compound
10. 10
    AutreFurther purification

Mode opératoire

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.

Source