反应详情

温度

100 °C

A mixture of 4-dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol (504 mg, 1.26 mmol), iodoaniline (331 mg, 1.51 mmol), [1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 171 mg, 0.25 mmol) and sodium carbonate (668 mg, 6.3 mmol) was evacuated for 30 min (oil pump). It was then flushed with argon and absolute N,N-dimethylformamide (5 mL, previously flushed for 1 h with argon) was added by syringe via a Schlenk tube. The mixture was stirred for 18 h at 100° C. and changed colour to dark brown during this. The reaction mixture was then concentrated to low volume in a vacuum, the residue taken up several times in toluol (3×10 mL) and concentrated to low volume again in each case, distributed between water and ethyl acetate (20 mL each) and the phases separated again. The aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organic phases were washed with 1 M sodium thiosulphate solution (30 mL) and saturated sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (750 mg) was purified by means of flash chromatography (38 g, 20×2.5 cm) with chloroform/methanol (97:3). The mixed fractions (489 mg) obtained were purified once again by means of MPLC [LiChroprep Si60 (15-25 μm), 130 g, 46×2.6 cm] also with chloroform/methanol (97:3).

1. customwas evacuated for 30 min (oil pump)
2. customIt was then flushed with argon and absolute N,N-dimethylformamide (5 mL
3. custompreviously flushed for 1 h with argon)
4. additionwas added by syringe via a Schlenk tube
5. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
6. concentrationconcentrated to low volume again in each case
7. customthe phases separated again
8. extractionThe aqueous phase was extracted with ethyl acetate (2×30 mL)
9. washthe combined organic phases were washed with 1 M sodium thiosulphate solution (30 mL) and saturated sodium chloride solution (50 mL)
10. dry with materialdried with sodium sulphate
11. concentrationconcentrated to low volume in a vacuum
12. customThe raw product (750 mg) was purified by means of flash chromatography (38 g, 20×2.5 cm) with chloroform/methanol (97:3)
13. customThe mixed fractions (489 mg) obtained
14. customwere purified once again by means of MPLC [LiChroprep Si60 (15-25 μm), 130 g, 46×2.6 cm] also with chloroform/methanol (97:3)