Diisobutylaluminumhydride → 2-[4-(6-Chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]ethanol

Participants

Reaction Conditions

Reaction Steps

Ethyl[4-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]acetate (150 mg, 0.56 mmol) (Example 413, Step 2) was taken up in THF (2.8 ml) and cooled to 0° C. Diisobutyl aluminum hydride (1.7 ml of 1.0M in hexanes, 1.7 mmol) was added dropwise over 15 minutes, and the reaction was maintained at 0° C. for 30 minutes. The reaction was allowed to warm to room temperature and maintained at room temperature for 20 hours. The mixture was then quenched with saturated aqueous potassium sodium tartrate and stirred for 2 hours. Ethyl acetate (10 mL) was added, and the mixture was stirred for 1 hour, after which product was extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-5% methanol/ethyl acetate) to afford the title compound.

Provenance & Evidence