Hydrochloric Acid → 4-Chloro-2-methoxy-1,3-thiazole-5-carbaldehyde

Participants

Reaction Steps

5N HCl (10 ml) is added to a solution of 4-chloro-5-([1,3]dioxolan-2-yl)-2-methoxy-thiazole (1.80 g, 8.13 mmol) in tetrahydrofuran (50 ml). After 1 h, the reaction is poured into 2N NaOH (100 ml) and extracted with ethyl acetate (3×100 ml). The ethyl acetate is washed with aqueous saturated brine solution, dried with anhydrous Na2SO4, filtered, and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes to yield (1.30 g, 90%) of 4-chloro-2-methoxy-thiazole-5-carboxaldehyde: mass spectrum (ion spray): m/z=178.0 (M+1); 1H NMR (CDCl3): δ=9.95 (1H, s), 4.22 (3H, s).

Provenance & Evidence