反应详情

To a solution of ethyl 3-(chloromethyl)-2-(3-cyanophenyl)-2-methylcyclopropanecarboxylate (Preparation 35, 5.82 g, 21.1 mmol) in N,N-dimethylformamide (20 ml) at room temperature was added sodium hydrogen carbonate (1.77 g, 21.1 mmol) followed by hexylamine (16.7 ml, 0.13 mol). The mixture was then heated under reflux for 16 h, cooled to room temperature and poured onto ice. After warming to room temperature, the mixture was partitioned against diethyl ether (50 ml). The two layers were separated and the aqueous layer was extracted with diethyl ether (2×30 ml). The ethereal extracts were washed with water (50 ml), dried (MgSO4), filtered and concentrated in vacuo. The crude oil was purified by silica column chromatography eluting with a gradient of hexane:ethyl acetate (5:1 to 0:100) to afford the title compound (2.2 g, 35%) as a colourless oil.

1. temperatureThe mixture was then heated
2. temperatureunder reflux for 16 h
3. additionpoured onto ice
4. temperatureAfter warming to room temperature
5. customthe mixture was partitioned against diethyl ether (50 ml)
6. customThe two layers were separated
7. extractionthe aqueous layer was extracted with diethyl ether (2×30 ml)
8. washThe ethereal extracts were washed with water (50 ml)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe crude oil was purified by silica column chromatography
13. washeluting with a gradient of hexane:ethyl acetate (5:1 to 0:100)