反应详情

温度

85 °C

To a solution of 3-Iodo-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester (15 g, 46.6 mmol) and prop-2-yn-1-ol (5.22 g, 93 mmol) in Acetonitrile (100 mL) was added Pd(PPh3)2Cl (3.27 g, 4.66 mmol), copper(I) iodide (0.89 g, 4.66 mmol) and triethylamine (14 g, 140 mmol). The mixture was heated at 85° C. reflux under N2 for 3 hrs. The reaction was cooled to room temperature, and concentrated to dryness, which was diluted with H2O (50 mL), extracted with ethyl acetate (200 mL×3), The organic phase was washed with saturated aqueous NaHCO3 150 mL, dried over Na2SO4, After concentration, the crude product was purified by silica gel chromatography eluted with PE:EtOAc=10:1-4:1 to give afford title product (8.5 g, 73% yield) as yellow oil. LCMS (m/z) ES+=233 (M+1).

1. temperaturereflux under N2 for 3 hrs
2. temperatureThe reaction was cooled to room temperature
3. concentrationconcentrated to dryness, which
4. additionwas diluted with H2O (50 mL)
5. extractionextracted with ethyl acetate (200 mL×3)
6. washThe organic phase was washed with saturated aqueous NaHCO3 150 mL
7. dry with materialdried over Na2SO4
8. concentrationAfter concentration
9. customthe crude product was purified by silica gel chromatography
10. washeluted with PE
11. customEtOAc=10:1-4:1 to give