반응 #50760

반응 방정식

1,2-dibromoethane

2-benzenesulphonyl-5-methoxytetrahydrofuran

Magnesium

4-bromoveratrole

→

2-(3,4-dimethoxyphenyl)-5-methoxytetrahydrofuran

수율 82.0%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   온도with warming
2. 2
   기타reaction
3. 3
   온도The resulting solution was heated
4. 4
   온도at reflux for 0.75 h
5. 5
   workup.STIRRINGto stir at room temperature for 20 h
6. 6
   기타Reaction
7. 7
   기타was quenched by addition of 1N HCl (50 ml)
8. 8
   추출extracted with ether (2×100 ml)
9. 9
   세척The organics were combined washed with water (50 ml)
10. 10
    건조dried over anhydrous sodium sulphate
11. 11
    여과filtered
12. 12
    기타evaporated

실험 절차

Magnesium (2.18 g, 0.091M) was placed in a 3-necked flask containing dry THF (10 ml) and 1,2-dibromoethane (0.2 ml). A solution of 4-bromoveratrole (18.0 g, 0.086M) in THF (50 ml) was added dropwise, with warming to initiate reaction. The resulting solution was heated at reflux for 0.75 h then cooled to room temperature and cannulated into a 1M solution of ZnBr2 in THF (50 ml, 0.05M) and stirred for 0.5 h at room temperature. A solution of 2-benzenesulphonyl-5-methoxytetrahydrofuran (10.0 g, 0.041M) in THF (50 ml) was added dropwise to the pale yellow suspension and the mixture allowed to stir at room temperature for 20 h. Reaction was quenched by addition of 1N HCl (50 ml), and extracted with ether (2×100 ml). The organics were combined washed with water (50 ml) dried over anhydrous sodium sulphate, filtered and evaporated. Column chromatography (flash silica gel; 3:2 hexane/ethyl acetate) gave 2-(3,4-dimethoxyphenyl)-5-methoxytetrahydrofuran (8.0 g, 82%) as a yellow oil (rf 0.28).

출처