反应详情

温度

-78 °C

A solution of 7-bromo-4,4-dimethyl-chroman (1.0 g, 4.15 mmole) in 20 mL of THF at −78° C., was treated with 1.91 mL of 2.5M butyllithium. After 30 minutes at −78° C. a solution of hexanoic acid methoxy-methyl-amide (0.726 g, 4.56 mmole) in 5 mL of THF was added. The reaction mixture was stirred at −78° C. for 30 minutes, warmed to room temperature, quenched by the addition of 25 mL 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 0.516 g of 1-(4,4-dimethyl-chroman-7-yl)-hexan-1-one as a colorless oil.

1. temperaturewarmed to room temperature
2. customquenched by the addition of 25 mL 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)