反应详情

K2CO3 (1.92 g, 13.9 mmol, 100 mol %) was added to N,N′-bis(2-methyl-2-triphenylmethylthiopropyl)ethylenediamine (10.03 g, 13.9 mmol) in CH3CN (60 mL), followed by ethyl 5-bromovalerate (3.30 mL, 20.8 mmol, 150 mol %). The reaction was heated at reflux under argon overnight. The solution was then concentrated to a paste and partitioned between 0.25 M KOH (100 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (1×50 mL) and the combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2×50 mL), dried with Na2SO4 and concentrated to an orange oil. Purification by flash chromatography (300 g flash silica, 100% CHCl3 to 5% MeOH/CHCl3) gave pure title compound (7.75 g, 66% yield). FABMS analysis yielded an (MH+) of 849 (compared with a calculated molecular weight of 849.24 for the compound C55H64N2O2S2).

1. temperatureThe reaction was heated
2. temperatureat reflux under argon overnight
3. concentrationThe solution was then concentrated to a paste
4. custompartitioned between 0.25 M KOH (100 mL) and ethyl acetate (100 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (1×50 mL)
6. washthe combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2×50 mL)
7. dry with materialdried with Na2SO4
8. concentrationconcentrated to an orange oil
9. customPurification by flash chromatography (300 g flash silica, 100% CHCl3 to 5% MeOH/CHCl3)