反应详情

(Method F) Lithium acetylide ethylenediamine complex (305 mg, 3.3 mmol, 1.1 equiv.) was placed in a three-neck flask, degassed, flushed with N2 and suspended in DMSO (2 ml). To the stirred suspension a solution of 3-[(7-bromoheptyl)oxy]benzenecarboxamide (943 mg, 3 mmol, 1 equiv.) in DMSO (2 ml), was added, slowly, dropwise, at r.t., under N2. The reaction mixture was stirred at r.t. for 16 h. After that time it was diluted with 1N HCl solution and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography on silica eluting with EtOAc/hexane 20%, to give the desired compound as a white solid (100 mg, 13%), mp 82-83° C. HPLC-MS (method 1): m/z 260 [M+H]+, Rt=4.26 min.

1. customdegassed
2. customflushed with N2
3. customat r.t.
4. extractionextracted with EtOAc (×3)
5. washThe combined organic extracts were washed with brine
6. dry with materialdried (Na2SO4)
7. customevaporated to dryness under reduced pressure
8. customThe crude product was purified by column chromatography on silica eluting with EtOAc/hexane 20%