반응 #2692

반응 방정식

carbon dioxide

methyl iodide

potassium carbonate

n-Butyllithium

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole

→

4-Methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)

용매

DMF

ether

반응 조건

후처리

1. 1
   workup.ADDITIONfilled
2. 2
   기타reaction flask
3. 3
   workup.STIRRINGafter stirring overnight
4. 4
   여과the ether was filtered off
5. 5
   세척The solid residue was washed with chloroform
6. 6
   기타dried under vacuum
7. 7
   workup.STIRRINGwas stirred for 1.5 h at 60° C
8. 8
   workup.WAITThe stirring was continued overnight
9. 9
   여과The mixture was filtered
10. 10
    기타the solution evaporated
11. 11
    workup.DISSOLUTIONthe residue was dissolved in dichloromethane
12. 12
    세척The organic phase was washed with water (2*30 mL)
13. 13
    건조dried (Na2SO4)
14. 14
    기타evaporated
15. 15
    기타to give
16. 16
    기타after additional drying under vacuum a bright green-yellow crystalline pure product

실험 절차

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole (2.0 g, 6.98 mmol) was dissolved in dry ether (50.0 mL) in a dry, argon filled reaction flask. n-Butyllithium (3.07 mL, 2.5M in hexane) was added and the reaction mixture was stirred for 30 min. The solution was poured onto solid carbon dioxide and, after stirring overnight, the ether was filtered off. The solid residue was washed with chloroform and dried under vacuum. The crude product was mixed with potassium carbonate (0.97 g, 6.98 mmol) in dry DMF (20.0 mL) and was stirred for 1.5 h at 60° C. After cooling to ambient temperature, methyl iodide (0.435 mL, 6.98 mmol) was added. The stirring was continued overnight. The mixture was filtered, the solution evaporated and the residue was dissolved in dichloromethane and water. The organic phase was washed with water (2*30 mL), dried (Na2SO4) and evaporated to give after additional drying under vacuum a bright green-yellow crystalline pure product.

출처