Methanol → 2-(2-Chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Dimethyl-1-diazo-2-oxypropylphosphonate (0.48 g, 2.5 mmol) was added to a solution of 2-(2-chloro-3-formyl-phenoxy)-butyronitrile (0.4 g, 1.8 mmol) in MeOH (40 ml) at room temperature under argon. The solution was cooled to 0° C. and K2CO3 was added. After the addition stirring was continued for 48 h at room temperature. Reaction mixture was then poured into cold water (0° C.) and extracted twice with ethylacetate. The combined organic layers were dried with MgSO4 and evaporated. The crude product was chromatographed on silica with ethylacetate/cyclohexane to yield 2-(2-chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester (0.32 g, light yellow oil); 1H-NMR (CDCl3) 1.05 t, 3H, 1.85-2.03 m, 2H, 3.39, s, 1H, 4.52 dd, 1H, 6.78 d, 1H, 7.12 t, 1H, 7.19 d, 1H, 7.72, br s, 1H.

Provenance & Evidence