3-Bromodiphenyl ether → (1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

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Reaction Steps

(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate was prepared using a procedure analogous to (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate except that 1-bromo-3-phenoxybenzene was replaced with 2-methyl-4-phenylthiazole. The title compound was obtained (0.125 g, 0.266 mmol, 62.1% yield) as a light yellowish oil. LCMS, [M+H]+=470.1. 1H NMR (500 MHz, CDCl3) δ 7.77-7.72 (m, 2H), 7.43-7.32 (m, 7H), 3.75 (s, 2H), 3.66 (s, 2H), 2.64 (s, 3H), 2.45 (s, 3H), 2.08-1.99 (m, 2H), 1.82 (ddd, J=13.3, 11.6, 4.3 Hz, 2H), 1.61 (qd, J=7.2, 3.0 Hz, 2H), 1.43 (td, J=12.4, 4.8 Hz, 2H).

Provenance & Evidence