反应详情

To a solution of NaOH (1.69 g, 42.2 mmol) in H2O (11 mL) was added a solution of triethylene glycol monomethyl ether (5.00 mL, 31.9 mmol) in THF (11 mL) under nitrogen, while the temperature was maintained below 5° C. by cooling with an ice-salt bath. At the same temperature, a solution of p-toluenesulfonyl chloride (6.08 g, 31.9 mmol) in THF (13 mL) was added dropwise over 1 h. The reaction mixture was poured into water and DCM was added. The layers were separated, and the aqueous layer was extracted with DCM (three times). The combined organic layers were washed with water (twice) and brine (twice), dried over anhydrous MgSO4, filtered off and evaporated to dryness to give 16 (8.43 g, 83%): 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=8.3 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 4.16 (t, 2H), 3.50-3.70 (m, 10H), 3.32 (s, 3H), 2.40 (s, 3H).

1. temperaturewhile the temperature was maintained below 5° C.
2. temperatureby cooling with an ice-salt bath
3. additionwas added
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with DCM (three times)
6. washThe combined organic layers were washed with water (twice) and brine (twice),
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered off
9. customevaporated to dryness