Water → HCID 67957761, compound

Participants

Reaction Steps

In an oven-dried placed flask under a nitrogen atmosphere, the product of Step 3 (150 g), phenylboronic acid (45 g) and sodium carbonate (85 g) were stirred in 1,2-dimethoxyethane (750 mL) and deionized water (225 mL). A nitrogen purge line was inserted directly into the reaction mixture for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (10 g) was added and the reaction mixture heated to reflux for 4.5 hours. After cooling to room temperature, the reaction mixture was slowly poured into a beaker containing deionized water (1.5 L) and ice while stirring. Concentrated hydrochloric acid was added until the pH reached 3. A separatory funnel was used to perform chloroform extractions (3×600 mL). The recovered organic layers were combined, washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate and concentrated by rotary evaporation. The resulting residue was purified by column chromatography on silica gel (400 g) eluting with a solution of 30% ethyl acetate/70% hexanes. Fractions containing product were combined and concentrated by rotary evaporation yielding methyl 1-([1,1′-biphenyl]-4-yl)-4-acetoxy-7-methoxy-2-naphthoate (149 g).

Provenance & Evidence