반응 #160677

반응 방정식

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

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

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도cooled
2. 2
   workup.ADDITIONare dropped
3. 3
   workup.STIRRINGunder stirring
4. 4
   기타The phases are separated
5. 5
   추출the aqueous layer is extracted three times with dichloromethane
6. 6
   세척The combined organic extracts are washed with saturated sodium hydrogencarbonate solution
7. 7
   건조dried over magnesium sulfate
8. 8
   기타the solvents are removed under reduced pressure
9. 9
   기타to give 150 g of the crude title compound
10. 10
    기타Further purification

실험 절차

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.

출처