반응 #68396

반응 방정식

2-butyramido-4-nitrophenyl trifluoromethanesulfonate

Compound 118

2-butyramido-4-nitrophenyl trifluoromethanesulfonate

3-methyl-1-butyne

→

title compound

N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

용매

CH3CN

Et3N

반응 조건

후처리

1. 1
   기타was purged with N2 for 10 min
2. 2
   기타the mixture was purged with N2 for another 5 min
3. 3
   기타the reaction was quenched with aqueous NaHCO3
4. 4
   추출extracted with EtOAc (×3)
5. 5
   세척The combined organic layer was washed with brine
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

실험 절차

A mixture of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (Compound 118, 200 mg, 0.56 mmol), CuI (32 mg, 0.17 mmol), and n-Bu4NI (311 mg, 0.84 mmol) in CH3CN (5 ml) and Et3N (1 ml) was purged with N2 for 10 min and Pd(PPh3)4 (64 mg, 0.056 mmol) was added and the mixture was purged with N2 for another 5 min. The mixture was then cooled to 0° C. and 3-methyl-1-butyne (76 mg, 1.12 mmol) was added. After 5 min, the reaction was quenched with aqueous NaHCO3, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes) to yield the title compound.

출처