2-Methyl-4-phenyl-1,3-thiazole → 4-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane

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Reaction Steps

4-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane was prepared using a procedure analogous to 5-(4-(iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole except that 2-methyl-4-phenylthiazole was replaced with 2-(3-bromophenoxy)tetrahydro-2H-pyran. The title compound was obtained (1.2 g, 2.80 mmol, 100% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.24 (t, J=8.0 Hz, 1H), 7.14-7.11 (m, 1H), 7.02 (ddd, J=7.8, 1.6, 1.0 Hz, 1H), 6.96 (ddd, J=8.2, 2.5, 0.9 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 4.00-3.87 (m, 3H), 3.62 (dtd, J=11.3, 4.1, 1.2 Hz, 1H), 3.08 (s, 2H), 2.16-1.98 (m, 5H), 1.93-1.58 (m, 9H).

Provenance & Evidence