反应详情

Phenylmagnesium bromide (3.0M solution in diethyl ether) (271 mL), was added dropwise to a stirred (overhead stirrer) solution of cycloheptanecarbonitrile (50 g) in 229 mL diethyl ether under nitrogen at such a rate as to maintain gentle reflux. The reaction mixture was then heated at reflux for 3 hours. TLC indicated no starting material present in the reaction mixture. The reaction mixture was allowed to cool to room temperature and stood under nitrogen overnight. The reaction mixture was cooled to 0° C. and treated dropwise with 102 mL 4N HCl(aq) keeping the temperature below 20° C. 4N sulfuric acid (203 mL) was added dropwise rapidly to start with and then more slowly towards the end. The ice bath was removed and the diethyl ether was distilled off. The reaction mixture was heated at 80-90° C. for 3.5 hours then allowed to cool to room temperature and stood overnight. The mixture was diluted with ether (approx 450 mL) and water (100 mL). The layers were separated and the aqueous layer was extracted with ether (2×400 mL). The organic layers were combined and washed with saturated aqueous sodium hydrogen carbonate (600 mL) and brine (600 mL), dried over magnesium sulphate, filtered and evaporated to give the sub-titled compound as an orange liquid (86.5 g).

1. temperatureto maintain gentle reflux
2. temperatureThe reaction mixture was then heated
3. temperatureat reflux for 3 hours
4. temperatureThe reaction mixture was cooled to 0° C.
5. customthe temperature below 20° C
6. customThe ice bath was removed
7. distillationthe diethyl ether was distilled off
8. temperatureThe reaction mixture was heated at 80-90° C. for 3.5 hours
9. temperatureto cool to room temperature
10. waitstood overnight
11. additionThe mixture was diluted with ether (approx 450 mL) and water (100 mL)
12. customThe layers were separated
13. extractionthe aqueous layer was extracted with ether (2×400 mL)
14. washwashed with saturated aqueous sodium hydrogen carbonate (600 mL) and brine (600 mL)
15. dry with materialdried over magnesium sulphate
16. filtrationfiltered
17. customevaporated