Sodium borohydride → {4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-methanol

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Reaction Steps

Sodium borohydride (0.127 g, 3.35 mmol) was added to a solution of 4-[4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethyl-benzaldehyde (0.370 g, 8.4 mmol) in 10 ml of methanol. After stirring 30 minutes, the reaction was quenched by addition of 1 ml of brine. The solvent was removed in vacuo, and the residue was extracted with methylene chloride/brine (10 ml of each). The aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford an oil (490 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=1:1 in volume) yielded the title compound (380 mg) as an oily colorless solid.

Provenance & Evidence