Benzenesulfinic acid, sodium salt → Methyl 4-[5-methyl-4-[(phenylsulfonyl)methyl]-1,3-oxazol-2-yl]benzoate

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Reaction of chloride 2 (267 mg, 1.0 mmol) and sodium benzenesulfinate (173 mg, 1.1 mmol) gave benzoate 16 (311 mg, 84%) as a white powder: mp (EtOAc) 159-161° C.; 1H NMR (CDCl3) δ 8.07 (ddd, J=8.7, 1.9, 1.5 Hz, 2H, H-2, H-6), 7.91 (ddd, J=8.7, 1.9, 1.5 Hz, 2H, H-3, H-5), 7.82 (ddd, J=8.2, 2.0, 1.2 Hz, 2H, H-2′, H-6′), 7.64 (tt, J=7.5, 1.2 Hz, 1H, H-4′), 7.52 (br dd, J=8.2, 7.5 Hz, 2H, H-3′, H-5′), 4.32 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.32 (s, 3H, CH3); MS m/z 372.3 (MH+, 100%). Anal. calcd for C19H17NO5S: C, 61.44; H, 4.61; N, 3.77. Found: C, 61.75; H, 4.62; N, 3.75%.

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