反応 #2692

反応方程式

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)

溶媒

DMF

ether

反応条件

後処理

1. 1
   workup.ADDITIONfilled
2. 2
   その他reaction flask
3. 3
   workup.STIRRINGafter stirring overnight
4. 4
   ろ過the ether was filtered off
5. 5
   洗浄The solid residue was washed with chloroform
6. 6
   その他dried under vacuum
7. 7
   workup.STIRRINGwas stirred for 1.5 h at 60° C
8. 8
   workup.WAITThe stirring was continued overnight
9. 9
   ろ過The mixture was filtered
10. 10
    その他the solution evaporated
11. 11
    workup.DISSOLUTIONthe residue was dissolved in dichloromethane
12. 12
    洗浄The organic phase was washed with water (2*30 mL)
13. 13
    乾燥dried (Na2SO4)
14. 14
    その他evaporated
15. 15
    その他to give
16. 16
    その他after additional drying under vacuum a bright green-yellow crystalline pure product

実験手順

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.

出典