반응 #64636

반응 방정식

4-tert-butylphenylethyne

4-tert-butylphenyl ethyne

Compound 19

4-tert-butylphenyl ethyne

ethyl-6-chloronicotinate

Compound 54

ethyl-6-chloronicotinate

→

title compound

Ethyl-6-(4-tert-butylphenylethynyl)nicotinate

용매

triethylamine

반응 조건

후처리

1. 1
   기타was degassed under nitrogen
2. 2
   온도The mixture was then heated at 65 degrees C
3. 3
   workup.WAITfor 12 hours
4. 4
   온도cooled to room temperature
5. 5
   기타the excess triethylamine removed under vacuum
6. 6
   추출extracted with ether
7. 7
   기타The solvent was then removed in-vacuo
8. 8
   기타the residue purified by flash chromatography (silica 5% ethyl acetate in hexane)

실험 절차

A mixture of 477.7 mg (3.02 mmol) of 4-tert-butylphenylethyne (Compound 19), 556.5 mg (3.01 mmol) of ethyl-6-chloronicotinate (Compound 54), 27.8 mg (0.15 mmol) of cuprous iodide, 58.7 mg (0.08 mmol) of bis(triphenylphosphine)palladium (II) chloride and 2 ml of triethylamine was degassed under nitrogen and then stirred under nitrogen at room temperature for 40 hours. The mixture was then heated at 65 degrees C. for 12 hours, cooled to room temperature and the excess triethylamine removed under vacuum. The residue was taken up in water and extracted with ether. The solvent was then removed in-vacuo and the residue purified by flash chromatography (silica 5% ethyl acetate in hexane) to give the title compound as a pale brown solid. PMR (CDCl3): & 1.33 (9H, s), 1.42 (3H, t, J~7.1 Hz); 4.42 (2H, q, J~7.1 Hz), 7.40 (2H, d, J~8.4 Hz), 7.53-7.61 (3H, m), 8.28 (1H, dd, J~8.1 Hz, 2.0 Hz), 9.20 (1H, d, J~2.0 Hz).

출처