反应详情

A mixture of 5-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (4.0 g, 13 mmol), sodium pentafluoropropionate (4.85 g, 26 mmol), copper (I) iodide (5.22 g, 27.2 mmol), toluene (70 ml) and dimethylformamide (70 ml) was heated under argon with Dean-Stark distillation (70 ml distillate collected), then heated at reflux for 18 h. The mixture was cooled, then poured into a mixture of water (150 ml) and 0.880 ammonia (150 ml). Resulting solution was extracted with dichloromethane (4×100 ml) and the combined extracts dried (Na2SO4) and evaporated in vacuo to give a solid. Chromatography on silica with 10-50% ether-hexane gradient elution gave the title compound (2.97 g, 66%) as a colourless solid.

1. temperaturewas heated under argon with Dean-Stark distillation (70 ml distillate collected)
2. temperatureheated
3. temperatureat reflux for 18 h
4. temperatureThe mixture was cooled
5. extractionResulting solution was extracted with dichloromethane (4×100 ml)
6. dry with materialthe combined extracts dried (Na2SO4)
7. customevaporated in vacuo
8. customto give a solid
9. washChromatography on silica with 10-50% ether-hexane gradient elution