反应详情

温度

-40 °C

To a solution of 2-(5-bromopyrid-3-yl)cyclohexanone (1.28 g, 5.05 mmol) in dry tetrahydrofuran (35 ml) at -40° C. was added portionwise with stirring potassium tert. butoxide (0.61 g, 5.4 mmol). The reaction mixture was stirred for 1 hour at -40° C. and a solution of carbon disulphide (0.5 ml) in dry tetrahydrofuran (5 ml) was added and the reaction mixture allowed to warm up to -20° C. over 20 minutes. A solution of methyl iodide (1.03 g) in dry tetrahydrofuran (5 ml) was added dropwise and the solution stirred at room temperature for 6 hours. The reaction mixture was concentrated in vacuo, treated with water (25 ml) and extracted with dichloromethane (2×25 ml). The extract was washed with water, dried over magnesium sulphate and concentrated to give 2-(5-bromopyrid-3-yl)-2-methylthiothiocarbonylcyclohexanone as an orange oil 1.33 g. NMR (CDCl3) 1.6-2.1(m,4H); 2.26-2.35(m,2H); 2.6 (s,3H); 2.65-2.9(m.1H); 3.4-3.5(m,1H), 7.84-7.86(dd,1H); 8.54-8.6(dd,2H).

1. temperatureto warm up to -20° C. over 20 minutes
2. stirringthe solution stirred at room temperature for 6 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. additiontreated with water (25 ml)
5. extractionextracted with dichloromethane (2×25 ml)
6. washThe extract was washed with water
7. dry with materialdried over magnesium sulphate
8. concentrationconcentrated