反応 #160677

反応方程式

hydrochloric acid

3,4-dimethoxy-ω-nitrostyrene

2-trimethylsilyloxy-1,3-butadiene

Toluene

→

title compound

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

溶媒

ethyl acetate

反応条件

後処理

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

実験手順

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.

出典