Trimethylsilyldiazomethane → Methyl 4-cyano-2-ethoxybenzoate

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Reaction Steps

Crude 4-cyano-2-ethoxybenzoic acid (19 g) was dissolved in a mixture of benzene (446 mL) and methanol (111 mL). At 0° C., (trimethylsilyl)diazomethane (76 mL, 2.0 M in ether, Aldrich) was added slowly and then at room temperature. Solvent was removed, and the residue was purified by flash chromatography (silica gel, eluting with 25% ethyl acetate in hexane) to give 4-cyano-2-ethoxybenzoic acid methyl ester as a solid (15.5 g, 74%).

Provenance & Evidence