反应详情

[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester (500 mg, 1.6 mmol) was added to an ice cold solution of iodomethane (100 μl, 1.7 mmol) and sodium hydride (73 mg, 1.7 mmol; 55% suspension in mineral oil) in DMF (5 ml). The reaction mixture was stirred for 5 h at ambient temperature, cooled to 0° C. and carefully quenched with saturated aqueous ammonium chloride solution. Ice water/ethyl acetate 1/1 were added, the layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined extracts were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, heptane/AcOEt) to give 258 mg (0.8 mmol, 49%) of the title compound as yellow oil.

1. temperaturecooled to 0° C.
2. customcarefully quenched with saturated aqueous ammonium chloride solution
3. additionIce water/ethyl acetate 1/1 were added
4. customthe layers were separated
5. extractionthe aqueous layer was extracted two times with ethyl acetate
6. washThe combined extracts were washed with brine
7. dry with materialdried over sodium sulfate
8. customThe solvent was removed under reduced pressure
9. customthe residue was purified by flash chromatography (silica gel, heptane/AcOEt)