反应详情

A solution of 0.5M ZnCl2 in THF (60 mL, 30 mmol) in THF (20 mL) at room temperature was treated with 2M ethyl magnesium chloride in THF (15 mL, 30 mmol) dropwise via syringe, cooled with an ice bath for about 10 minutes, stirred at room temperature for 20 minutes, cooled to 0° C., and treated sequentially with Pd(PPh3)4 (1.73 g, 1.5 mmol) and a solution of 4-nitrobenzoyl chloride (6.12 g, 33 mmol) in THF (20 mL). The mixture was stirred at 0° C. for 40 minutes, diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with saturated Na2CO3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate to provide 2.17 g (40%) of the desired product. Rf=0.6 (3:1 hexanes/ethyl acetate).

1. temperaturecooled with an ice bath for about 10 minutes
2. temperaturecooled to 0° C.
3. stirringThe mixture was stirred at 0° C. for 40 minutes
4. extractionextracted three times with ethyl acetate
5. washThe combined extracts were washed with saturated Na2CO3, water, and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate