反应详情

温度

25 °C

A solution of 23 (0.435 g 1.43 mmol) in 5.7 mL anhydrous THF was cooled to −25° C. and treated with TMEDA (0.758 mL, 5.0 mmol) followed by n-BuLi (2.29 mL of a 2.5 M solution in hexane, 5.0 mmol) in a slow dropwise manner. The resulting gold solution was stirred for 2 h at −25° C. The reaction mixture was treated with 1-chloro-2-iodoethane (0.37 mL, 5.0 mmol) and stirred for 15 min at 25° C. The reaction was diluted with H2O (40 mL), extracted with Et2O (3×20 mL), and the combined organic extracts were washed with saturated aqueous NaCl, dried Na2SO4) and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5×15 cm, 0-7% EtOAc/hexane gradient) yielded 24 (490 mg, 80%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 8.03 (d, J=12.8 Hz, 1H), 7.78 (d, J=12.5 Hz, 1H), 7.42 (m, 2H), 7.14 (br s, 1H), 5.20 (s, 2H), 3.74 (s, 3H), 1.56 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 154.7, 152.6, 135.1, 134.8, 127.6, 127.4, 125.1, 125.0, 122.2, 113.0, 100.5, 87.7, 81.1, 58.5, 28.4; IR (film) νmax 3391, 2977, 2933, 1732, 1524, 1367, 1340, 1276, 1228, 1157 cm−1; FABHRMS (NBA/NaI) m/z 430.0507 (C17H20INO4+H+ requires 430.0515).

1. extractionextracted with Et2O (3×20 mL)
2. washthe combined organic extracts were washed with saturated aqueous NaCl, dried Na2SO4) and
3. concentrationconcentrated under reduced pressure