Water → (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate

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Reaction Steps

Sodium methoxide (0.725 g, 13 mmol) and methyl formate (0.8 ml, 13 mmol) were added portionwise to a stirred solution of methyl 2-(6-trifluoromethylpyrid-2-yloxymethyl)phenylacetate (2.0 g, 6.0 mmol) in dry toluene (15 ml) under a nitrogen atmosphere at room temperature. After 6 hours at room temperature, the mixture was poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and the ether removed to give (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (2.01 g, 95%) as a yellow gum which was used in the next stage without further purification; 1H NMR (270 MHz)δ: 3.75(3H,s), 5.34(2H,s), 6.90(1H,d), 7.15-7.75(7H,m), 11.95(1H,d) ppm.

Provenance & Evidence