反应详情

温度

0 °C

To a suspension of 2-naphthylmethyl ethanimidothioate hydrobromide (3.0 g, 0.01 mol) in THF (20.0 mL) at 0° C., is added N-methylmorpholine (2.4 mL. 0.022 mol), followed by the dropwise addition of a solution of methyl malonyl chloride (1.2 mL, 0.011 mol) in THF (5.0 mL). The resulting mixture is stirred at 0° C. for 30 min, and at room temperature for an additional 30 min. The mixture is diluted with cold water, (25 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts are washed with water, dried (Na2SO4), filtered and concentrated to dryness under reduced pressure to give a yellow syrup, which is purified by flash chromatography using 25% EtOAc in hexanes to give the title compound (1.9 g, 59%) as colorless syrup: ES-HR MS m/z 316.0993 (M+H calcd for C17H18NO3SN requires 316.1002).

1. waitat room temperature for an additional 30 min
2. extractionextracted with dichloromethane (2×20 mL)
3. washThe combined organic extracts are washed with water
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure
7. customto give a yellow syrup, which
8. customis purified by flash chromatography