Benzyl Chloride → 1-Phenyl-3-(phenylmethoxy)-1H-indole-2-carboxylic acid methyl ester

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A mixture of 1.2 g (0.025 mole) of 50% sodium hydride/mineral oil suspension in 20 ml of hexamethylphosphoramide under a nitrogen atmosphere was cooled in ice and treated over 15 minutes with a solution of 5.3 g (0.020 mole) of 3-hydroxy-1-phenyl-1H-indole-2-carboxlic acid methyl ester [P. Friedlander and K. Kurz, Chem. Ber., 55, 1597 (1922)] in 25 ml of hexamethylphosphoramide. The mixture was stirred in ice an additional one hour, 2.6 ml (2.9 g, 0.023 mole) of benzyl chloride was added in one portion, the ice bath was removed and stirring was continued for a total of 18 hours. The reaction mixture was added to 200 g of ice/water, stirred for one hour, and the precipitated product was filtered and washed with water. Recrystallization from aqueous methanol yielded 3.8 g (54% yield) of the ester product. An additional recrystallization as above yielded analytically pure ester, mp 117°-119° C.

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