反应详情

Four ml of a 3M (12 mmol) solution of ethylmagnesium bromide in ether is placed in a 3-necked flask fitted with a mechanical stirrer, a reflux condenser protected by a drying tube and a pressure-equalizing dropping funnel protected by a drying tube. The flask is cooled in an ice-bath and a solution of 3.174 g (10 mmol) of 2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl] pyridine-5-carboxaldehyde in 10 ml of dry ether is added slowly with vigorous stirring. The cooling bath is then removed and the mixture heated at reflux for 3 hours. The mixture is then cooled in an ice-salt bath and 5 ml of saturated ammonium chloride solution is added. The mixture is stirred for a further 1 hour and then filtered and the residue washed with two 10 ml portions of ether. The ether solution is then separated, dried (MgSO4) and the ether removed in vacuo. The residue is then purified by chromatography followed by recrystallization to give the title compound.

1. customfitted with a mechanical stirrer, a reflux condenser
2. customprotected by a drying tube
3. customprotected by a drying tube
4. temperatureThe flask is cooled in an ice-bath
5. customThe cooling bath is then removed
6. temperaturethe mixture heated
7. temperatureat reflux for 3 hours
8. temperatureThe mixture is then cooled in an ice-salt bath
9. addition5 ml of saturated ammonium chloride solution is added
10. filtrationfiltered
11. washthe residue washed with two 10 ml portions of ether
12. customThe ether solution is then separated
13. dry with materialdried (MgSO4)
14. customthe ether removed in vacuo
15. customThe residue is then purified by chromatography
16. customfollowed by recrystallization