反应详情

温度

55 °C

To a solution of 2-(2-tert-butoxycarbonyl-ethyl)-5-hydroxy-benzoic acid 2-trimethylsilanyl-ethyl ester (4.30 g, 11.7 mmol) and toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester (4.61 g, 12.9 mmol) in DMF (30 mL) was added Cs2CO3 (4.59 g, 14.1 mmol). The suspension was stirred at 55° C. for 12 h. The reaction mixture was quenched with H2O (200 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried (Na2SO4) and concentrated to a residue, which was purified using silica gel chromatography (hexanes/EtOAc 9/1 to 8/2) to afford the title compound as a colorless oil (5.04 g, 78%). 1H NMR (400 MHz, CDCl3): δ 0.06 (s, 9H), 1.11 (t, 2H, J=8.8 Hz), 1.40 (s, 9H), 2.36 (s, 3H), 2.51 (t, 1H, J=7.8 Hz), 2.97 (t, 2H, J=6.8 Hz), 3.12 (t, 1H, J=7.8 Hz), 4.24 (t, 2H, J=6.8 Hz), 4.35 (t, 2H, J=8.8 Hz), 6.88 (dd, 1H, J=3.0, 8.3 Hz), 7.15 (d, 1H, J=8.3 Hz), 7.37-7.44 (m, 4H), 7.97 (d, 2H, J=7.8 Hz).

1. customThe reaction mixture was quenched with H2O (200 mL)
2. extractionextracted with EtOAc (3×100 mL)
3. dry with materialThe combined organics were dried (Na2SO4)
4. concentrationconcentrated to a residue, which
5. customwas purified