反应详情

温度

0 °C

An oven-dried 100 mL pear-shaped flask, fitted with an oven-dried stir bar, was charged with a 0.5 M solution of 1-propynyl magnesium bromide in THF (12.5 mL, 6.27 mmol) via cannula. The solution was cooled to 0° C., and then a solution of 28.2 (1.05 g, 2.85 mmol) in anhydrous THF (6 mL) was added over 3 minutes via cannula. The reaction was stirred at 0° C. for 5 minutes and then stirred at room temperature for 1.5 hours. The reaction mixture was poured into saturated NH4Cl(aq) and extracted with ethyl acetate. The combined organic layers were washed with water, followed by brine. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes) followed by recrystallization from hot ethyl acetate and hexanes to yield 162 mg (15%) of 2,2-Dimethyl-5-{1-[4-(2-methyl-benzylsulfanyl)-phenyl]-but-2-ynyl}-[1,3]dioxane-4,6-dione (28.3). LC/MSD m/e: 409.1 (M+H).

1. customAn oven-dried 100 mL pear-shaped flask, fitted with an oven-dried
2. stirringThe reaction was stirred at 0° C. for 5 minutes
3. stirringstirred at room temperature for 1.5 hours
4. extractionextracted with ethyl acetate
5. washThe combined organic layers were washed with water
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes)
9. customfollowed by recrystallization from hot ethyl acetate and hexanes