Boron Trichloride → 6-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol

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Reaction Conditions

Reaction Steps

Dissolve (2,6-dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (56.0 g, 123 mmol) in chloroform (500 mL). Cool to 0° C. Add boron trichloride (150 mL, 150 mmol, 1 M solution in dichloromethane) and stir 2 hours. Warm to room temperature and stir 1.5 hours. Add additional boron trichloride (50 mL, 50 mmol) after cooling to 0° C. Warm to room temperature and stir overnight. Carefully add ice and saturated aqueous sodium bicarbonate. Separate organic and wash aqueous three times with a 3:1 dichloromethane:isopropanol mixture. Concentrate in vacuo and dissolve in dichloromethane. Dry over sodium sulfate, decant, and concentrate in vacuo. Slurry in ether and filter, rinsing with hexanes to give 49.4 g of (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (99%).

Provenance & Evidence