反应详情

A mixture of Zn—Cu couple (2.68 g, 41.3 mmol) and tert-butyl(3-iodopropoxy)dimethylsilane (8.26 g, 27.5 mmol) in benzene (55 mL) and DMF (3.6 mL) was stirred vigorously at room temperature for 1 hour, heated to 60° C. for 4 hours, cooled to room temperature, and treated with a solution of 4-nitrobenzoyl chloride (3.4 g, 18.3 mmol) and (Ph3P)4Pd (0.847 g, 0.73 mmol) in benzene (36 mL) by cannula. The mixture was stirred for 1 hour, filtered through diatomaceous earth (Celite™), and partitioned between saturated NH4Cl and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes to provide 2.81 g of the desired product. MS(ESI(−)) m/e 322 (M−H)−.

1. temperatureheated to 60° C. for 4 hours
2. temperaturecooled to room temperature
3. stirringThe mixture was stirred for 1 hour
4. filtrationfiltered through diatomaceous earth (Celite™)
5. custompartitioned between saturated NH4Cl and ethyl acetate
6. extractionThe aqueous phase was extracted three times with ethyl acetate
7. washthe combined extracts were washed with water and brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes