Hexane → Thiazole, 2-methyl-4-(2-phenylethynyl)-

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Reaction Steps

1-Chloro-4-phenyl-3-butyn-2-one (1.6 g, 9.1 mmol) was dissolved in dry acetonitrile (15 mL), treated with thioacetamide (680 mg, 9.1 mmol), and heated to reflux for 4 h. After cooling, the acetonitrile was removed in vacuo, and the residue was partitioned between water (50 mL) and ethyl acetate (150 mL). The organic phase was dried over Na2SO4, filtered, concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography on silica gel eluting with 99:1, 98:2, then 95:5 hexane:ethyl acetate to afford 2-methyl-4-(phenylethynyl)-1,3-thiazole (240 mg, 13% yield) as a red oil. 1H NMR (CDCl3, 300 MHz) δ 7.58–7.54 (m, 2H), 7.40–7.34 (m, 4H), 2.74 (s, 3H). MS (EI ionization) 199 (M+).

Provenance & Evidence