反应详情

温度

-78 °C

A solution of 7-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.08 g, 0.15 mmole) in 2 mL of THF at −78° C. was treated with 0.13 mL of 2.5M butyllithium. The reaction mixture was stirred at −78° C. for 1 hour, then at room temperature for 2 hours, quenched by the successive addition of 5 mL water and 5 mL of saturated aqueous ammonium chloride solution and extracted with three 25 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes) to yield 0.049 g of 4,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as a colourless oil.

1. waitat room temperature for 2 hours
2. customquenched by the successive addition of 5 mL water and 5 mL of saturated aqueous ammonium chloride solution
3. extractionextracted with three 25 mL portions of ether
4. dry with materialThe combined organic extracts were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a yellow oil
8. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes)