Imidazole → Tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilane

Participants

Reaction Steps

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.

Provenance & Evidence