Reaction #160677

Reaction equation

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

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

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   workup.ADDITIONare dropped
3. 3
   workup.STIRRINGunder stirring
4. 4
   OtherThe phases are separated
5. 5
   Extractionthe aqueous layer is extracted three times with dichloromethane
6. 6
   WashThe combined organic extracts are washed with saturated sodium hydrogencarbonate solution
7. 7
   Dryingdried over magnesium sulfate
8. 8
   Otherthe solvents are removed under reduced pressure
9. 9
   Otherto give 150 g of the crude title compound
10. 10
    OtherFurther purification

Procedure

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