2-Acetyl-4-methylthiazole → 2-(4-Methyl-1,3-thiazol-2-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethynylmagnesium bromide (0.5 M in THF, 30.6 mL, 15.30 mmol) maintained under nitrogen at −20° C. was added slowly a solution of 1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one (1.8 g, 10.20 mmol, 80%) in tetrahydrofuran (10 mL) over a period of 20 min. The resulting solution was stirred for 3 hr at 20-30° C. and then quenched by the addition of water (20 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1/6) to yield 0.5 g (26%) of the title compound as a yellow solid: LC-MS: m/z=+168 (M+H)+.

Provenance & Evidence