Sodium p-toluenesulfinate → Methyl 4-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoate

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Reaction Steps

A mixture of chloride 2 (1.54 g, 5.8 mmol) and sodium 4-methylbenzenesulfinate (1.08 g, 6.1 mmol) gave benzoate 3 (1.96 g, 88%) as a white powder: mp (EtOAc) 177-178° C.; 1H NMR (CDCl3) δ 8.08 (ddd, J=8.7, 2.0, 1.6 Hz, 2H, H-2, H-6), 7.92 (ddd, J=8.7, 2.0, 1.6 Hz, 2H, H-3, H-5), 7.69 (ddd, J=8.3, 1.9, 1.7 Hz, 2H, H-2′, H-6′), 7.30 (br d, J=8.3 Hz, 2H, H-3′, H-5′), 4.29 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.43 (s, 3H, CH3), 2.31 (s, 3H, CH3); MS m/z 386.5 (MH+, 100%). Anal. calcd for C20H19NO5S: C, 62.32; H, 4.97; N, 3.63. Found: C, 62.59; H, 4.96; N, 3.71%.

Provenance & Evidence