Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate → Methyl 4-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate

Participants

Reaction Steps

Method A. Reaction of chloride 2 (268 mg, 1.0 mmol) and sodium 4-chlorobenzenesulfinate (198 mg, 1.0 mmol) gave benzoate 19 (273 mg, 67%) as a white powder: mp (EtOAc) 186-188° C.; 1H NMR (CDCl3) δ 8.08 (ddd, J=8.7, 1.9, 1.6Hz, 2 H, H-2, H-6), 7.90 (ddd, J=8.7, 1.9, 1.6Hz, 2 H, H-3, H-5), 7.74 (ddd, J=8.7, 2.4, 2.0Hz, 2 H, H-2′, H-6′), 7.49 (ddd, J=8.7, 2.4, 2.0Hz, 2 H, H-3′, H-5′), 4.32 (s, 2 H, CH2SO2), 3.94 (s, 3 H, OCH3), 2.37 (s, 3 H, CH3); MS m/z 407.0 (MH+, 100%), 409.0 (MH+, 35%). Anal. calcd for C19H16ClNO5S: C, 56.23; H, 3.97; N, 3.45. Found: C, 56.11; H, 3.80; N, 3.35%.

Provenance & Evidence