Trimethylsilyldiazomethane → Methyl 3-(3-hydroxypropyl)-4,5-dimethoxybenzoate

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Reaction Steps

To a stirred solution of 3-(3-hydroxypropyl)-4,5-dimethoxybenzoic acid (Example 10, Step 1, 3.53 g, 14.7 mmol) in MeOH (37 mL) at 0° C. was slowly added trimethylsilyldiazomethane (TMSCHN2) (2.0 M, 37 mL, 73.5 mmol) over the course of 5 min. After stirring for 10 min the reaction mixture was concentrated. The crude product was purified by flash column chromatography on silica gel using 67% EtOAc in hexanes as an eluent to furnish 3-(3-hydroxypropyl)-4,5-dimethoxybenzoic acid methyl ester (2.76 g).

Provenance & Evidence