反应详情

温度

175 °C

28.9 g (322 mmol) of copper(I) cyanide was added to 22.7 g (80.7 mmol) of 2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 270 mL of N-methyl pyrrolidine. The reaction mixture was heated at 175° C. After 16 hours, the mixture was cooled to room temperature and treated with 400 mL of 10% aqueous ammonium hydroxide. The reaction mixture was filtered to remove salts and the solids were extracted with hot ethyl acetate. The combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The product was purified by gradient elution through a pad of silica gel (hexane-5% ethyl acetate/hexane) to give 18 g (95%) of 2-cyano-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (M+=227).

1. temperaturethe mixture was cooled to room temperature
2. filtrationThe reaction mixture was filtered
3. customto remove salts
4. extractionthe solids were extracted with hot ethyl acetate
5. washThe combined organic fractions were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe product was purified by gradient elution through a pad of silica gel (hexane-5% ethyl acetate/hexane)