반응 #72076

반응 방정식

DMF

(trimethylsilyl)acetylene

ethyl 3-bromo-6-nitro-1-benzothiophene-2-carboxylate

Ethyl 3-bromo-6-nitro-1-benzothiophene-2-carboxylate

→

title compound

Ethyl 6-nitro-3-[(trimethylsilyl)ethynyl]-1-benzothiophene-2-carboxylate

용매

triethylamine

반응 조건

후처리

1. 1
   농축The reaction solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   세척washed with dilute hydrochloric acid and brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   농축concentration under reduced pressure
6. 6
   기타the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10)
7. 7
   기타recrystallized from an ethyl acetate/hexane solvent

실험 절차

DMF (20 ml), (trimethylsilyl)acetylene (5 ml), triethylamine (10 ml) and bis(triphenylphosphine)palladium (II) dichloride (420 mg, 0.6 mmol) were added to ethyl 3-bromo-6-nitro-1-benzothiophene-2-carboxylate obtained in Example (183b) (794 mg, 2.41 mmol) and copper (I) iodide (12 mg, 0.63 mmol), and the mixture was stirred at 80° C. for one hour. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with dilute hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10) and recrystallized from an ethyl acetate/hexane solvent, to obtain 110 mg of the title compound as crystals.

출처