反应详情

Under a nitrogen atmosphere, p-toluenesufonyl chloride (7.01 g, 36.77 mmol) was added to a stirring solution of (2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol (3.00 g, 18.38 mmol) in dry triethylamine (20 mL) at 0° C. After stirring and warming to ambient temperature over 18 h, the mixture was stirred with cold, saturated NaHCO3 solution (50 mL) for 1 hour and extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford a thick, dark-brown mass (˜7 g). The crude product was purified by column chromatography on silica gel, eluting with chloroform-acetone (98:2, v/v) to afford 4.00 g (68.6%) of a light-brown syrup.

1. extractionextracted with chloroform (3×50 mL)
2. dry with materialThe combined chloroform extracts were dried (K2CO3)
3. filtrationfiltered
4. concentrationconcentrated by rotary evaporation
5. customto afford a thick, dark-brown mass (˜7 g)
6. customThe crude product was purified by column chromatography on silica gel
7. washeluting with chloroform-acetone (98:2