Ethyl 4-chloroacetoacetate → Ethyl (2-methyl-1,3-thiazol-4-yl)acetate

Participants

Reaction Steps

Prepare a solution of thioacetamide (10 g, 133 mmol) in ethanol (75 mL). Add ethyl-4-chloroacetoacetate (16.5 mL, 122 mmol). Stir the reaction overnight at 50° C. and then concentrate in vacuo. Dissolve the resulting oil in water (75 mL) and extract with diethyl ether (3×50 mL). Extract the aqueous layer with CHCl3 (3×50 mL). Wash the combined organic layers with brine (50 mL), dry (Na2SO4), filter, and concentrate in vacuo to afford (2-methylthiazol-4-yl)acetic acid ethyl ester (17 g) as a solid. 1H NMR (CDCl3) δ 7.02 (s, 1H), 4.15-4.25 (m, 2H), 3.79 (s, 2H), 2.71 (s, 3H), 1.25 (t, J=7 Hz, 3H).

Provenance & Evidence