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

Participants

Reaction Conditions

Reaction Steps

Dissolve (2,6-dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in CH2Cl2 (10 volume eq.) in a 3-neck round bottom flask equipped with a pressure equalizing addition funnel, stirbar, and N2 source. Cool the flask in an ice/brine bath and add 1.0 M BCl3 solution in CH2Cl2 (1.2 eq.) dropwise. The reaction solution turns dark red and the temperature initially increases to 5° C. After about 1 hour, quench the reaction with methanol (5 eq.) and allow to warm to room temperature. Dilute the organic solution with CH2Cl2 (one volume eq.) and add a 1.0 M NaHCO3 solution (5 volume eq.) and stir for one hour. Separate the aqueous and organic layers. Wash the aqueous layer with CH2Cl2 (one volume) and combine the organic layers. Wash with saturated. NH4Cl and dry over Na2SO4. Purify the product via column chromatography (50/1 silica gel) eluting with CH2Cl2/hexanes (3/1) to yield (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone.

Provenance & Evidence