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0 °C

A mixture of 0.90 g (2.52 mmol) of ethyl 4-chloro-6-[4-formylphenoxy)-1-methyl-2-indolecarboxylate, 0.10 g (2.52 mmol) of sodium borohydride and 20 ml of ethanol was stirred at 0° C. for 2 hours. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.91 g (>99%) of ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate.

1. additionThe reaction mixture was poured onto ice water
2. extractionThe resulting mixture was then extracted three times with ethyl acetate
3. washThe combined extracts were washed with saturated sodium chloride aqueous solution
4. dry with materialAfter drying over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure