Methyl iodide → 2-(2-Methoxybut-3-yn-2-yl)-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (I-1) (1.0 g, 6.33 mmol) in DMF (15 mL) cooled to 0° C., was slowly added sodium hydride (60% oil dispersion) (0.30 g, 7.6 mmol). After stirring at 0° C. for 20 min, methyl iodide (0.47 mL, 7.6 mmol) was added. The solution was warmed to RT. The mixture was partition between EtOAc (50 mL) and water (20 mL). The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (Isolute column, 20% EtOAc in heptane) gave the title compound as a pale yellow oil: 1H NMR (250 MHz, CDCl3) δ 1.91 (3H, s), 2.78 (1H, s), 3.41 (3H, s), 7.35 (1H, d, J=3.20 Hz), 7.80 (1H, d, J=3.20 Hz); LC-MS: m/z=+167.9 (M+H)+.

Provenance & Evidence