反应详情

温度

-78 °C

To 3.0 ml of 1M lithium aluminum hydride (3.0 mmol) in THF, cooled to -78° C., was added dropwise over 5 min a solution of 2.0 g (5.9 mmol) of ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)-ethynyl)nicotinate in 5 ml of THF. The reaction mixture was stirred at -78° C. for 40 rain and then treated with 2 ml of water. The mixture was warmed to room temperature and the organic layer was separated. The aqueous layer was extracted with 3×10 ml of ether. The organic extracts were combined and washed successively with 1×10 ml of dilute HCl, 3×10 ml of water and 1×15 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 50% ethyl acetate in hexanes) to give the title compound as a pale yellow solid.

1. temperatureThe mixture was warmed to room temperature
2. customthe organic layer was separated
3. extractionThe aqueous layer was extracted with 3×10 ml of ether
4. washwashed successively with 1×10 ml of dilute HCl, 3×10 ml of water and 1×15 ml of saturated NaCl solution
5. dry with materialdried (MgSO4)
6. customThe solvent was removed in vacuo
7. customthe residue purified by flash chromatography (silica; 50% ethyl acetate in hexanes)