反应详情

Iodination of alcohol 169 with I2, PPh3 and imidazole as in Example 2GGG above for 12 h, followed by chromatography of the product on silica gel, eluting with 0-5% CH2Cl2/petroleum ether (foreruns) and then with 5-10% CH2Cl2/petroleum ether, gave tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilane (171) (94%) as a colourless oil; 1H NMR (CDCl3) δ 7.55 (dt, J=9.0, 2.7 Hz, 2H), 6.68 (dt, J=9.0, 2.7 Hz, 2H), 3.98 (dd, J=9.4, 5.7 Hz, 1H), 3.92 (dd, J=9.4, 6.2 Hz, 1H), 3.74 (dd, J=10.1, 5.6 Hz, 1H), 3.69 (dd, J=10.1, 5.6 Hz, 1H), 3.38 (dd, J=10.0, 5.9 Hz, 1H), 3.35 (dd, J=10.0, 6.1 Hz, 1H), 2.09 (sept, J=5.8 Hz, 1H), 0.89 (s, 9H), 0.06 (2 s, 6H); HRFABMS calcd for C16H27I2O2Si m/z [M+H]+ 532.9870. found 532 9864.

1. customabove for 12 h
2. washeluting with 0-5% CH2Cl2/petroleum ether (foreruns)