Sodium hydride → 3-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxy-pyridine-2carboxylic acid methyl ester (200 mg) in DMF (2.0 ml) was added at 22° C. NaH (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0° C. and treated with trifluoroethyl trifluormethane-sulphonate (728 mg) and stirring was continued at 22° C. for 2 h. The mixture was partitioned between saturated NaHCO3 and ethyl acetate and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane/ethyl acetate (3:1) to give 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester as a pale green oil. MS (ISP): m/z=236.2 [M+H]+.

Provenance & Evidence