反应详情

温度

-40 °C

A solution of methyl 4-(2-((1R,2S)-2-((E)-3-((tert-butyldimethylsilyl)oxy)-4-(naphthalen-2-yl)but-1-en-1-yl)-5-oxocyclopent-3-en-1-yl)ethyl)benzoate (111 mg, 0.20 mmol) in toluene (1.6 mL) was added dropwise by cannula to a −40° C. mixture of [Ph3PCuH]6 (205 mg, 0.11 mmol) in toluene (9.8 mL), rinsing with 0.4 mL toluene. The reaction was stirred at −40° C. for 1 h and then at room temperature overnight. Saturated NH4Cl solution (20 mL) was added and the resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (91 mg, 82%).

1. washrinsing with 0.4 mL toluene
2. customat room temperature
3. customovernight
4. additionSaturated NH4Cl solution (20 mL) was added
5. extractionthe resulting mixture was extracted with ethyl acetate (3×20 mL)
6. dry with materialThe combined organic solution was dried (Na2SO4)
7. filtrationfiltered
8. customevaporated
9. customPurification by flash chromatography (ethyl acetate/hexanes)