反应详情

Anhydrous pyridine (0.15 mL) and toluene (10 mL) were added to 3a (249.0 mg, 0.578 mmol) and stirred at RT under dry argon. Docosahexaenoyl chloride (200.0 mg, 0.578 mmol) in toluene (5 mL) was then added dropwise to the reaction mixture over a period of 20 min and stirred at RT for 96 hours. The reaction mixture was poured into water (100 mL), extracted with diethyl ether (100 mL, 3×), washed successively with 0.25 M H2SO4 solution (100 mL), saturated aqueous NaHCO3 (100 mL) and water (100 mL), and dried over anhydrous Na2SO4. After removal of solvent, the crude product was chromatographed on silica gel using hexane-dichloromethane to obtain product 4a (348.4 mg, 81.4% yield). 1H NMR (in CDCl3): δ in ppm 0.89 (18H, m), 1.24 (29H, m), 1.53 (2H, m), 2.06 (2H, m), 2.40 (4H, m), 2.83 (10H, m), 3.40 (3H, m), 3.55 (2H, m), 3.71 (2H, m), 5.36 (12H, m); 13C NMR (in CDCl3): δ in ppm 14.2, 14.4, 20.7, 22.2, 25.7 (2), 25.8, 26.0, 26.1, 26.3, 29.5, 29.7, 29.8, 29.9, 32.0, 35.3, 65.4, 71.7, 72.9 (2), 127.1, 127.9, 128.0, 128.1, 128.2, 128.4, 128.5, 128.7, 129.2, 129.3, 130.1, 132.1, 168.8.

1. stirringstirred at RT for 96 hours
2. extractionextracted with diethyl ether (100 mL, 3×)
3. washwashed successively with 0.25 M H2SO4 solution (100 mL), saturated aqueous NaHCO3 (100 mL) and water (100 mL)
4. dry with materialdried over anhydrous Na2SO4
5. customAfter removal of solvent
6. customthe crude product was chromatographed on silica gel