反应详情

In a 3-neck, 2 L rbf, NaOH (135 g, 3.37 mol) was added slowly to water (1 L). After the addition was complete, the solution was cooled to room temperature and DCM (2 L) added, followed by triethylene glycol monoethyl ether (500 g, 2.81 mol). p-Toluenesulfonyl chloride (535 g, 2.81 mol) was added portion-wise over a period of 10 minutes, and the mixture refluxed for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (2 L), mixed well and separated. The organic phase was washed with water (2×2 L), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting clear, colourless oil was stirred at room temperature with a 10% aqueous NaOH solution (1 L) to hydrolyze unreacted p-toluenesulfonyl chloride. After 18 hours, the material was poured into water (1 L), extracted with chloroform (500 mL) and separated. The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L). The material was dried over anhydrous MgSO4, filtered and solvent removed by rotavap to afford (103) as a clear, colourless oil (595 g, 64%).

1. additionAfter the addition
2. temperaturethe mixture refluxed for 2 hours
3. temperatureAfter cooling to room temperature
4. additionmixed well
5. customseparated
6. washThe organic phase was washed with water (2×2 L)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customsolvent removed by rotary evaporation
10. additionthe material was poured into water (1 L)
11. extractionextracted with chloroform (500 mL)
12. customseparated
13. washThe organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L)
14. dry with materialThe material was dried over anhydrous MgSO4
15. filtrationfiltered
16. customsolvent removed by rotavap