反应详情

温度

-78 °C

A suspension of potassium bis(trimethylsilyl)amide (1.95 g, 0.0098 mole) in 20 mL of dry THF was treated with phenylacetylene (0.92 g, 0.009 mole). A flocculant white precipitate formed immediately. Benzoquinone (0.97 g, 0.009 mole) was dissolved in dry THF (10 mL) and cooled to -78° C. The potassium phenylacetylide generated above was added dropwise over a period of about 10 min. The reaction was stirred an additional 10 min, quenched by adding saturated ammonium chloride solution (20 mL) and allowed to warm to RT. The mixture was diluted with saturated ammonium chloride solution, extracted with ether and filtered to remove a flocculant dark brown precipitate. The phases were separated and the aqueous phase extracted with additional ether. The combined ether extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flask chromatography on silica gel using 4:1 hexane/EtOAc as the eluent and the fractions containing the title product were combined and concentrated in vacuo to yield 0.27 g (14%).

1. customA flocculant white precipitate formed immediately
2. additionabove was added dropwise over a period of about 10 min
3. customquenched
4. additionby adding saturated ammonium chloride solution (20 mL)
5. temperatureto warm to RT
6. additionThe mixture was diluted with saturated ammonium chloride solution
7. extractionextracted with ether
8. filtrationfiltered
9. customto remove a flocculant dark brown precipitate
10. customThe phases were separated
11. extractionthe aqueous phase extracted with additional ether
12. dry with materialThe combined ether extracts were dried over anhydrous sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe residue was purified by flask chromatography on silica gel using 4:1 hexane/EtOAc as the eluent
16. additionthe fractions containing the title product
17. concentrationconcentrated in vacuo
18. customto yield 0.27 g (14%)