Sodium Methoxide → HCID 68575204, compound

Participants

Reaction Steps

Sodium methoxide (0.63 g, 11.66 mmol) is added to a solution of 2,4-dichloro-5-([1,3]dioxolan-2-yl)-thiazole (2.00 g, 8.85 mmol) in methanol (20 ml). The reaction is heated at reflux for 3.5 h, cooled, and concentrated. The residue is partitioned between aqueous saturated brine solution and ethyl acetate, separated, and the aqueous layer extracted with ethyl acetate. The ethyl acetate is dried over Na2SO4, filtered, and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 12.5% ethyl acetate/hexanes to yield (1.12 g, 93%) of 4-chloro-5-([1,3]dioxolan-2-yl)-2-methoxy-thiazole: mass spectrum (ion spray): m/z=221.9 (M+1); 1H NMR (CDCl3): δ=6.05 (1H, s), 4.15-3.97 (7H, m).

Provenance & Evidence